Diisopropylethylamine → HCID 140484921, compound

HRID 1823207Notes

Reaction equation

HRID 1823207 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C:7](=[O:16])[N:8]2[C:12]=1[CH2:11][CH2:10][C@H:9]2[C:13](O)=[O:14])(=[O:3])[CH3:2].[C:28]([O:32][C:33](=[O:45])[NH:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([CH2:43][NH2:44])=[CH:39][CH:38]=1)=[NH:36])([CH3:31])([CH3:30])[CH3:29].C1CN([P+](ON2N=NC3C=CC=NC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:21]([O:20][C:18](=[O:19])[NH:17][C:6]1[C:7](=[O:16])[N:8]2[C:12](=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1)[CH2:11][CH2:10][C@H:9]2[C:13](=[O:14])[NH:44][CH2:43][C:40]1[CH:41]=[CH:42][C:37]([C:35]([NH:34][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:45])=[NH:36])=[CH:38][CH:39]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 11038641((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphateHCID 69549446HCID 69549446, compoundHCID 145832046tert-butyl N-[4-(aminomethyl)benzenecarboximidoyl]carbamate

Product 1

HCID 140484921HCID 140484921, compoundYield 48.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The acid (43 mg, 0.116 mmol) obtained from Step D was placed in a flask with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester (32 mg, 0.128 mmol), PyAOP (76 mg, 0.145 mmol) and dissolved in 2 mL DMF. DIEA (61 μL, 0.348 mmol) was added and the reaction allowed to stir for 2 h. The reaction was diluted with EtOAc and 5% NaHCO3 was added and stirred for 10 min. The phases were separated and the aqueous phase extracted 2× with EtOAc, dried with sodium sulfate and concentrated. Purified by HPLC and lyopholized to give the product as a white solid (34 mg, 41% yield). 1HNMR (300 MHz, CDCl3) δ 1.614 (s, 9H) 2.3 (m, 1H) 2.5 (s, 3H) 2.6 (m, 1H) 3.4–3.6 (m, 2H) 3.6–3.8 (m, 2H) 5.2 (m, 1H) 5.25 (s, 2H) 7.4 (m, 9H) 7.6 (m, 2H) 7.8 (m, 2H).

Workup

  1. additionwas added
  2. stirringstirred for 10 min
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted 2× with EtOAc
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customPurified by HPLC

Sources & evidence

ORD record
ord-20dd4721aafc4dd8bc6b873f5652019f
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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