N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-2-amine → HCID 178457481, compound

HRID 2169490Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([C:36](O)=[O:37])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:39]([O:46][CH2:47][CH2:48][NH:49][CH:50]([CH3:52])[CH3:51])([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].[Si](OCCN(C(C)C)C(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2(C3C=CC(C(F)(F)F)=CC=3)CCCC2)N=1)=O)(C(C)(C)C)(C)C>>[CH2:1]([O:8][C:9]1[C:10]([C:36]([N:49]([CH2:48][CH2:47][O:46][Si:39]([C:42]([CH3:44])([CH3:43])[CH3:45])([CH3:40])[CH3:41])[CH:50]([CH3:51])[CH3:52])=[O:37])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:23]=[C:24]([C:32]([F:34])([F:33])[F:35])[CH:25]=[C:26]([C:28]([F:29])([F:31])[F:30])[CH:27]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 57917054N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-2-amine

HCID 178457477HCID 178457477, compound

HCID 178524874HCID 178524874, compound

Product 1

HCID 178457481HCID 178457481, compound

Procedure

5-(Benzyloxy)-2-((1-(3,5-bis(trifluoromethyl)phenyl)cyclopentyl)methyl)-N-(2-((tert-butyl-dimethylsilyl)oxy)ethyl)-6-hydroxy-N-isopropylpyrimidine-4-carboxamide (463) was synthesized from 5-(benzyloxy)-2-((1-(3,5-bis(trifluoromethyl)phenyl)cyclopentyl)methyl)-6-hydroxypyrimidine-4-carboxylic acid (462) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (8b) following the procedure described for 5-benzyloxy-2-[1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (245).

Sources & evidence

ORD record: ord-29b0a5a0a16a49ff9a6f86717ec35243
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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