tert-Butyl 3-oxa-7,9-diazabicyclo(3.3.1)nonane-7-carboxylate → methyl (4R)-4-(2-bromo-4-fluoro-phenyl)-6-(3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-ylmethyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate

HRID 1778487Notes

Reaction equation

HRID 1778487 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[NH:16][CH:10]([CH2:11][O:12][CH2:13]2)[CH2:9]1)=O)(C)(C)C.[Br:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@H:25]1[C:30]([C:31]([O:33][CH3:34])=[O:32])=[C:29]([CH2:35]Br)[NH:28][C:27]([C:37]2[S:38][CH:39]=[CH:40][N:41]=2)=[N:26]1.COC(C1[C@H](C2C=CC(F)=CC=2Cl)N=C(C2SC=CN=2)NC=1CBr)=O>>[Br:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@H:25]1[C:30]([C:31]([O:33][CH3:34])=[O:32])=[C:29]([CH2:35][N:16]2[CH:14]3[CH2:15][NH:8][CH2:9][CH:10]2[CH2:11][O:12][CH2:13]3)[NH:28][C:27]([C:37]2[S:38][CH:39]=[CH:40][N:41]=2)=[N:26]1

Participants

4

Reactant 3

HCID 53415349tert-Butyl 3-oxa-7,9-diazabicyclo(3.3.1)nonane-7-carboxylateHCID 89995948Methyl (R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateHCID 117706695(R)-methyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate2×

Product 1

HCID 117706699methyl (4R)-4-(2-bromo-4-fluoro-phenyl)-6-(3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-ylmethyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate

Procedure

Compound 53b was prepared in analogy to intermediate AC in Example 15, starting from 3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester and methyl (4R)-4-(2-bromo-4-fluoro-phenyl)-6-(bromomethyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate 53a, while 53a was prepared in analogy to compound C in Example 1.

Sources & evidence

ORD record
ord-0c8b381b8e6740d5a87da19e3467a992
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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