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Triethylamine → HCID 69075315, compound

HRID 490271
Notes
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Reaction equation

HRID 490271 reaction equation
[C:1]([O:5][C:6](=[O:48])[NH:7][C@H:8]([CH2:23][NH:24][C@@H:25]([C:29]1[N:38]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:37](=[O:46])[C:36]2[C:31](=[CH:32][C:33]([Cl:47])=[CH:34][CH:35]=2)[N:30]=1)[CH:26]([CH3:28])[CH3:27])[CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:56]1([CH3:65])[CH:61]=[CH:60][C:59]([C:62](Cl)=[O:63])=[CH:58][CH:57]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:48])[NH:7][CH:8]([CH2:23][N:24]([CH:25]([C:29]1[N:38]([CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:37](=[O:46])[C:36]2[C:31](=[CH:32][C:33]([Cl:47])=[CH:34][CH:35]=2)[N:30]=1)[CH:26]([CH3:28])[CH3:27])[C:62]([C:59]1[CH:60]=[CH:61][C:56]([CH3:65])=[CH:57][CH:58]=1)=[O:63])[CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])([CH3:3])([CH3:4])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 69078749((S)-1-{[(R)-1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-methyl}-4-benzyloxycarbonylamino-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 69075315HCID 69075315, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of ((S)-1-{[(R)-1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-methyl}-4-benzyloxycarbonylamino-butyl)-carbamic acid tert-butyl ester (250 mg, 0.37 mmol) in toluene (4 mL) was added triethylamine (0.10 mL, 0.74 mmol) followed by dropwise addition of p-toluoyl chloride (0.049 mL, 0.37 mmol). The reaction mixture was heated to 80° C. for 18 h, then reflux for 4 h. The reaction mixture was allowed to cool to room temperature, quenched with saturated aqueous NaHCO3 (10 mL) and diluted with CH2Cl2 (10 mL). The extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (3:1 hexanes:ethyl acetate) to provide 235 mg (79%) of the title compound as a pale yellow powder. MS(ES+) m/e 794.2 [M+H]+.

Workup

  1. temperaturereflux for 4 h
  2. temperatureto cool to room temperature
  3. customquenched with saturated aqueous NaHCO3 (10 mL)
  4. additiondiluted with CH2Cl2 (10 mL)
  5. dry with materialThe extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (3:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-e9a33926e6ec47dba386599690a92f84
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528137B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes