Dimethylformamide → HCID 90415746, compound

HRID 869126Notes

Reaction equation

HRID 869126 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[C:10]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[C:11]([C:12]([NH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[O:21][CH3:22])=[O:13])=[C:5]2[N:4]=1.CN(C=O)C.O=S(Cl)[Cl:37]>C(Cl)Cl>[Cl:37][CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[C:10]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[C:11]([C:12]([NH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[O:21][CH3:22])=[O:13])=[C:5]2[N:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 90415997HCID 90415997, compound

Product 1

HCID 90415746HCID 90415746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 5-(hydroxymethyl)-N-(4-methoxy-3-pyridyl)-2-[(2,2,2-trifluoroacetyl)amino]pyrazolo[1,5-a]pyrimidine-3-carboxamide prepared in step 2 above (50 mg, 0.1219 mmol) and DMF (44.55 mg, 47.19 μL, 0.6095 mmol) were suspended in dry DCM (1.25 mL). SOCl2 (72.51 mg, 44.46 μL, 0.6095 mmol) was added dropwise and the resulting mixture was stirred at RT for ˜2 h. The bright yellow suspension was filtered and the collected solid was washed with DCM (1 mL) and ether (3×1 mL) to give a light yellow powder (49.6 mg). LC-MS (M+H)+ 429.1; 1H NMR (500 MHz, DMSO-d6) δ 11.78 (s, 1H), 10.60 (s, 1H), 9.63 (s, 1H), 9.50 (d, J=7.1 Hz, 1H), 8.71 (d, J=6.4 Hz, 1H), 7.80 (d, J=6.6 Hz, 1H), 7.62 (d, J=7.1 Hz, 1H), 5.07 (s, 2H), 4.34 (s, 3H).

Workup

  1. filtrationThe bright yellow suspension was filtered
  2. washthe collected solid was washed with DCM (1 mL) and ether (3×1 mL)

Sources & evidence

ORD record
ord-b09557689af34708b7b5c31e1b42a490
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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