Hydrochloric Acid → HCID 67114808, compound

HRID 388835Notes

Reaction equation

HRID 388835 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:11][CH2:10]3)[N:6]([C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C:21]4[C:22]([CH3:27])=[N:23][CH:24]=[N:25][CH:26]=4)=[O:20])=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.[ClH:28]>C1COCC1.C(OCC)C>[ClH:28].[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:11][CH2:10]3)[N:6]([C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C:21]4[C:22]([CH3:27])=[N:23][CH:24]=[N:25][CH:26]=4)=[O:20])=[CH:14][CH:13]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 51353041HCID 51353041, compound

Product 1

HCID 67114808HCID 67114808, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-[6-(3,5-dicyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]-4-methylpyrimidine-5-carboxamide (230 mg) from intermediate 30 (200 mg, 0.83 mmol) and intermediate 53 (350 mg, 2.49 mmol) as a pale yellow solid and dissolved in THF. Saturated HCl in diethyl ether was added to this solution at 0° C. and stirred for 15 min. Solid that separated out was filtered and dried to give the title compound (120 mg) as a yellow solid. M.P.: 192-197° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.92 (s, 1H), 9.16 (s, 1H), 8.94 (s, 1H), 8.75 (d, J 2.5, 1H), 8.27 (dd, J 2.6, 8.8, 1H), 7.76 (d, J 8.8, 1H), 5.82 (s, 1H), 2.70-2.62 (m, 1H), 2.61 (s, 3H), 1.92-1.84 (m, 1H), 0.95-0.85 (m, 4H), 0.70-0.58 (m, 4H). MS (m/z): 360.97 [M+H—HCl]+.

Workup

  1. customSolid that separated out
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-e068f8f8c167471690ee0637d2c51c6b
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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