4-tert-Butylcyclohexylamine → HCID 68871420, compound

HRID 1984853Notes

Reaction equation

HRID 1984853 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([OH:17])=O)[CH:9]=2)=[O:4].[C:24]([CH:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)([CH3:27])([CH3:26])[CH3:25].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>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15](=[O:17])[NH:34][CH:31]1[CH2:32][CH2:33][CH:28]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:29][CH2:30]1)[CH:9]=2)=[O:4]

Participants

6

Reactant 4

HCID 793964-tert-ButylcyclohexylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68869055HCID 68869055, compound

Product 1

HCID 68871420HCID 68871420, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-cyclopentylmethyl-isoquinoline-3,7-dicarboxylic acid 3-methyl ester (38 mg, 0.121 mmol) in DMF(1.5 mL) was treated with 4-tert-butylcyclohexylamine (0.028 g, 0.181 mmol), HBTU (69 mg, 0.181 mmol), and DIEA (0.075 mL, 0.424 mmol) by the General Procedure A to give 57 mg of the desired 7-(4-tert-butyl-cyclohexylcarbamoyl)-1-cyclopentylmethyl-isoquinoline-3-carboxylic acid methyl ester as a colorless oil. This was used directly for the next step without purification.

Sources & evidence

ORD record
ord-52f7ec57dccb4680ab5e12f1adac6771
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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