Diisopropylethylamine → HCID 117709962, compound

HRID 1778550Notes

Reaction equation

HRID 1778550 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:16][CH:15]2[NH:17][CH:11]([CH2:12][O:13][CH2:14]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][C:26]1[NH:31][C:30]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)=[N:29][C@@H:28]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=2[Cl:44])[C:27]=1[C:45]([O:47][CH3:48])=[O:46].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:10][CH:11]2[N:17]([CH2:25][C:26]3[NH:31][C:30]([C:32]4[S:33][CH:34]=[CH:35][N:36]=4)=[N:29][C@@H:28]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=4[Cl:44])[C:27]=3[C:45]([O:47][CH3:48])=[O:46])[CH:15]([CH2:14][O:13][CH2:12]2)[CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 89995948Methyl (R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateHCID 117706979HCID 117706979, compound

Product 1

HCID 117709962HCID 117709962, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-[7-(tert-butoxycarbonylamino)-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl]acetate 146a (0.1 g, 0.3 mmol) and methyl (4R)-6-(bromomethyl)-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate C (90 mg, 0.2 mmol), DIPEA (77.4 mg, 0.6 mmol) in DCM (5 mL) was stirred for 12 hours at room temperature. The mixture was concentrated to give crude methyl (4R)-6-[[7-(tert-butoxycarbonylamino)-7-(2-ethoxy-2-oxo-ethyl)-3-oxa-9-azabicyclo[3.3.1]nonan-9-yl]methyl]-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate 146b. MS: calc'd (MH+) 692, exp (MH+) 692.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-4fe0653f460c48b98bf3c2da7ae5bf36
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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