Hydrochloric Acid → HCID 52913616, compound

HRID 881050Notes

Reaction equation

HRID 881050 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[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:30])[CH2:20][C:21]4[N:22]=[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][N:24]5[CH:29]=4)=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.[ClH:31]>C1COCC1.C(OCC)C>[ClH:31].[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:10][CH2:11]3)[N:6]([C:12]3[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:30])[CH2:20][C:21]4[N:22]=[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][N:24]5[CH:29]=4)=[CH:16][CH:17]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52913617HCID 52913617, compound

Product 1

HCID 52913616HCID 52913616, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-[4-(3,5-dicyclopropyl-1H-pyrazol-1-yl)phenyl]-2-(imidazo[1,2-a]pyridin-2-yl)acetamide (56 mg) was prepared from intermediate 29 (79 mg, 0.45 mmol) and intermediate 12 (90 mg, 0.38 mmol) as a brown 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 (54 mg) as a pale-brown solid. M. P. 92-97° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.82 (s, 1H), 8.92 (d, J 6.7, 1H), 8.32 (s, 1H), 7.97-7.92 (m, 2H), 7.75 (d, J 8.7, 2H), 7.53 (d, J 8.7, 2H), 7.52-7.47 (m, 1H), 5.79 (s, 1H), 3.80 (s, 2H), 1.87-1.71 (m, 2H), 0.93-0.79 (m, 4H), 0.69-0.58 (m, 4H). MS (m/z): 398.24 [M+H−HCl]+.

Workup

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

Sources & evidence

ORD record
ord-e64dfa6c89774490a27030c130ad2765
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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