Hydrochloric Acid → HCID 86631267, compound

HRID 60202Notes

Reaction equation

Cl.C(OC([N:9]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[N:17]=[C:18]([NH:34][C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=3)[C:19]3[N:24]=[C:23]([CH2:25][C:26]4[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:33])[S:22][C:20]=3[N:21]=2)[CH2:10]1)=O)(C)(C)C>>[ClH:32].[Cl:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([Cl:32])[C:26]=1[CH2:25][C:23]1[S:22][C:20]2[N:21]=[C:16]([NH:15][CH2:14][C@@H:11]3[CH2:12][CH2:13][NH:9][CH2:10]3)[N:17]=[C:18]([NH:34][C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=3)[C:19]=2[N:24]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 685124643-{[2-(2,6-Dichloro-benzyl)-7-(4-trifluoromethyl-phenylamino)-thiazolo[5,4-d]pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86631267HCID 86631267, compoundYield 80.5%

Procedure

A solution of HCl (4 N in dioxane; 2 mL) and 3-{[2-(2,6-dichloro-benzyl)-7-(4-trifluoromethyl-phenylamino)-thiazolo[5,4-d]pyrimidin-5-ylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (50 mg, 0.08 mmol) was stirred at rt for 6 h. The mixture was filtered and the resulting solid was washed with Et2O (10 mL) to provided the title compound as yellow solid (19 mg, 43%). MS (ESI): mass calcd. for C24H21Cl2F3N6S, 552.1; m/z found, 553.1 [M+H]+. 1H NMR ((CD3)2SO): 9.98 (s, 1H), 8.89 (s, 1H), 8.21 (d, J=8.6 Hz, 2H), 7.77-7.32 (m, 5H), 5.87-5.78 (m, 1H), 4.67 (s, 2H), 4.17-3.93 (m, 4H), 3.77-3.63 (m, 2H), 2.96-2.84 (m, 1H), 2.05-1.95 (m, 1H), 1.73-1.59 (m, 1H).

Workup

filtrationThe mixture was filtered
washthe resulting solid was washed with Et2O (10 mL)

Sources & evidence

ORD record: ord-ab6b1bf6b9cd427c8d15a1ed0105ac53
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440978B2

Reaction notes

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