Diisopropylethylamine → HCID 68867964, compound

HRID 1984855Notes

Reaction equation

HRID 1984855 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:30](O)=[O:31])[N:20]=[C:21]3[CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:16][CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:34][O:35][C:36](=[O:43])[C@@H:37]([NH2:42])[C:38]([CH3:41])([CH3:40])[CH3:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:34][O:35][C:36](=[O:43])[C@@H:37]([NH:42][C:30]([C:19]1[N:20]=[C:21]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:22]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([C:12](=[O:13])[NH:11][CH:8]1[CH2:9][CH2:10][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)[CH:23]=2)=[O:31])[C:38]([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16217630Methyl L-tert-leucinate hydrochlorideHCID 68868389HCID 68868389, compound

Product 1

HCID 68867964HCID 68867964, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(4-tert-butyl-cyclohexylcarbamoyl)-1-cyclopentylmethyl-isoquinoline-3-carboxylic acid (65 mg, 0.148 mmol) in DMF(1.5 mL) was treated with (2S)-amino-3,3-dimethyl-butyric acid methyl ester HCL (35 mg, 0.193 mmol), HBTU (73 mg), and DIEA (0.106 mL) by the General Procedure A. The crude product was purified by flash column chromatography on silica gel using 88:12 Hexanes/EtOAc to give 18 mg of 2(S)-{[7-(4-tert-butyl-cyclohexylcarbamoyl)-1-cyclopentylmethyl-isoquinoline-3-carbonyl]-amino}3,3-dimethylbutyric acid methyl ester as a colorless oil. This was used for the next step.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel using 88:12 Hexanes/EtOAc

Sources & evidence

ORD record
ord-39a660db4965408f97a3aa76adae5f02
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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