Hydrochloric Acid → HCID 86695100, compound

HRID 1503923Notes

Reaction equation

[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[C:28]3[C:27]4[C@@H:26]([CH2:29][C:30](=[O:37])[NH:31][CH2:32][C:33](=[O:36])[NH:34][CH3:35])[CH2:25][CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH2:12][CH2:11]1)C(=O)OC(C)(C)C.[ClH:38]>ClCCl>[ClH:38].[CH3:35][NH:34][C:33](=[O:36])[CH2:32][NH:31][C:30](=[O:37])[CH2:29][C@H:26]1[CH2:25][CH2:24][C:23]2[S:22][C:21]3[N:20]=[CH:19][N:18]=[C:17]([O:16][CH:13]4[CH2:12][CH2:11][CH:10]([NH:2][CH3:1])[CH2:15][CH2:14]4)[C:28]=3[C:27]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl N-methyl-N-(4-[[(3R)-3-([[(methylcarbamoyl)methyl]carbamoyl]methyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (130 mg, 0.24 mmol, 1.00 equiv) in 5.5 mL of dichloromethane was added concentrated hydrochloric acid (0.5 mL) at 0° C. under nitrogen. The resulting solution was stirred for 2 h at 0° C. in a water/ice bath and concentrated under reduced pressure to afford N-methyl-2-[2-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-3-yl]acetamido]acetamide hydrochloride (105 mg, crude) as a yellow oil. MS: m/z 432 [M+H]+.

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3636cd9cdd1a476ebcfdce5300bfc16c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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