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Hydrochloric Acid → HCID 58484973, compound

HRID 1255441
Notes
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Reaction equation

HRID 1255441 reaction equation
Cl.Cl[C:3]1[N:4]=[CH:5][C:6]2[N:12]([CH3:13])[C:11](=[O:14])[C:10]3([CH2:16][CH2:15]3)[CH2:9][N:8]([C@@H:17]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]3)[C:7]=2[N:24]=1.[NH2:25][C:26]1[CH:37]=[CH:36][C:29]([C:30]([NH:32][CH:33]2[CH2:35][CH2:34]2)=[O:31])=[CH:28][C:27]=1[O:38][CH3:39]>C(O)C.O>[CH:33]1([NH:32][C:30](=[O:31])[C:29]2[CH:36]=[CH:37][C:26]([NH:25][C:3]3[N:4]=[CH:5][C:6]4[N:12]([CH3:13])[C:11](=[O:14])[C:10]5([CH2:15][CH2:16]5)[CH2:9][N:8]([C@@H:17]5[CH2:21][CH2:20][C:19]([F:22])([F:23])[CH2:18]5)[C:7]=4[N:24]=3)=[C:27]([O:38][CH3:39])[CH:28]=2)[CH2:34][CH2:35]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58484975HCID 58484975, compoundHCID 67447132HCID 67447132, compound

Product 1

HCID 58484973HCID 58484973, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962
Water
Solvent

Conditions

Temperature
85 °C

Procedure

Concentrated hydrochloric acid (45 μl) was added to a mixture of (R)-2′-chloro-9′-(3,3-difluorocyclopentyl)-5′-methyl-8′,9′-dihydrospiro[cyclopropane-1,7′-pyrimido[4,5-b][1,4]diazepin]-6′(5′H)-one (100 mg, 0.29 mmol) and 4-amino-N-cyclopropyl-3-methoxybenzamide (90 mg, 0.44 mmol) in ethanol (1.4 mL) and water (5.2 mL). The reaction mixture was heated to 85° C. and stirred for 18 hours. The reaction mixture was concentrated in vacuo. The residue was taken up with ethyl acetate, washed with an aqueous saturated solution of sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the desired compound as a white solid (49 mg, 33% yield).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with an aqueous saturated solution of sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-688d92ea916f468ab236f6aab1f68076
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461149B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes