Diisopropylethylamine → HCID 178494455, compound

HRID 2202294Notes

Reaction equation

HRID 2202294 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[F:26][C:27]1[CH:28]=[C:29]([NH:38][C:39]([C@H:41]2[C:50]3[C:45](=[CH:46][C:47]([CH2:51][O:52][CH3:53])=[CH:48][CH:49]=3)[CH2:44][CH2:43][NH:42]2)=[O:40])[CH:30]=[C:31]2[C:35]=1[C:34]([CH3:37])([CH3:36])[CH2:33][CH2:32]2.[C:54]([O:58][C:59](=[O:68])[CH2:60][C@H:61]1[CH2:64][C@H:63]([C:65](O)=[O:66])[CH2:62]1)([CH3:57])([CH3:56])[CH3:55].CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:26][C:27]1[CH:28]=[C:29]([NH:38][C:39]([C@H:41]2[C:50]3[C:45](=[CH:46][C:47]([CH2:51][O:52][CH3:53])=[CH:48][CH:49]=3)[CH2:44][CH2:43][N:42]2[C:65]([C@H:63]2[CH2:62][C@H:61]([CH2:60][C:59]([O:58][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:68])[CH2:64]2)=[O:66])=[O:40])[CH:30]=[C:31]2[C:35]=1[C:34]([CH3:37])([CH3:36])[CH2:33][CH2:32]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118622789(R)-N-(7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)-6-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamide hydrochlorideHCID 178451084HCID 178451084, compound

Product 1

HCID 178494455HCID 178494455, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (49.9 mg, 0.13 mmol) was added to a solution of (R)—N-(7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)-6-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamide hydrochloride (50 mg, 0.12 mmol), trans-3-(2-(tert-butoxy)-2-oxoethyl)cyclobutanecarboxylic acid (26.9 mg, 0.13 mmol) and DIEA (0.024 mL, 0.13 mmol) in DMF (2 mL) at room temperature, and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the precipitate was collected by filtration, and washed with water to give tert-butyl 2-(trans-3-((R)-1-((7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)carbamoyl)-6-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)cyclobutyl)acetate (74.0 mg, 0.128 mmol, 107%) as a white solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-3e0990b6fb9448f7a05c9a3e582a010e
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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