Trifluoroacetic acid → (RS) 2-(4-chlorophenoxymethyl)-4-[(piperidin-3-yl)methoxy]-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole

HRID 1383995Notes

Reaction equation

[Cl:1][C:2]1[CH:49]=[CH:48][C:5]([O:6][CH2:7][C:8]2[N:12]([CH2:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)[C:11]3[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH2:34][CH:35]4[CH2:40][CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36]4)[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[N:12]([CH2:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[CH2:17]3)[C:11]3[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH2:34][CH:35]4[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]4)[C:10]=3[N:9]=2)=[CH:48][CH:49]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 21188665(RS) 2-(4-chlorophenoxymethyl)-4-[[1-(t-butoxycarbonyl)piperidin-3-yl]methoxy]-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole

Product 1

HCID 21188730(RS) 2-(4-chlorophenoxymethyl)-4-[(piperidin-3-yl)methoxy]-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole

Procedure

The title product is prepared from (RS) 2-(4-chlorophenoxymethyl)-4-[[1-(t-butoxycarbonyl)piperidin-3-yl]methoxy]-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole using a standard trifluoroacetic acid deprotection protocol.

Sources & evidence

ORD record: ord-8c82f4ec64d2477584afe79d85a20f62
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255494B1

Reaction notes

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