Methanol → HCID 178497577, compound

HRID 1484885Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:16][C:17]2[NH:21][N:20]=[C:19]([CH:22]3[CH2:24][CH2:23]3)[CH:18]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.O=S(Cl)Cl.[CH3:29]O>>[ClH:1].[Cl:1][C:2]1[C:3]([NH:16][C:17]2[NH:21][N:20]=[C:19]([CH:22]3[CH2:23][CH2:24]3)[CH:18]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([C:13]([O:15][CH3:29])=[O:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 178524249HCID 178524249, compound2×

Product 1

HCID 178497577HCID 178497577, compound

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-(5-chloro-4-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2-carboxylic acid (Compound 156) (50 mg, 0.138 mmol) in methanol (5 mL) was added SOCl2 (0.5 mL) dropwise. The mixture was stirred at 70° C. for 2 hrs. LCMS showed that the reaction is over. The solvent was removed in vacuum to the target product Methyl 5-(5-chloro-4-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2-carboxylate hydrochloride (Compound 154) as HCl salt (25 mg, 44%). LC-MS (m/z)=376 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.77-0.81 (m, 2H), 1.00-1.05 (m, 2H), 1.95-2.02 (m, 1H), 3.86 (s, 3H), 6.43 (s, 1H), 7.81-7.84 (m, 2H), 8.51 (s, 1H), 9.67 (s, 1H).

Workup

customThe solvent was removed in vacuum to the target product Methyl 5-(5-chloro-4-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2-carboxylate hydrochloride (Compound 154) as HCl salt (25 mg, 44%)

Sources & evidence

ORD record: ord-38b008ec524f4f68a87d4065835090a2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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