Hydrochloric Acid → HCID 10178676, compound

HRID 1392984Notes

Reaction equation

HRID 1392984 reaction equation
[BH4-].[Na+].[C:3]([C:11]1[CH:32]=[CH:31][C:14]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[N:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]4=[N:24][CH:23]=3)[CH:19]=[CH:18][N:17]=2)=[CH:13][CH:12]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CO>[OH:10][CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:11]1[CH:32]=[CH:31][C:14]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[N:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]4=[N:24][CH:23]=3)[CH:19]=[CH:18][N:17]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10157263HCID 10157263, compound

Product 1

HCID 10178676HCID 10178676, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (9 mg, 0.24 mmol) was added in one portion to a suspension of 2-(4-benzoylanilino)-4-(imidazo-[1,2-a]-pyridin-3-yl)-pyrimidine (27 mg, 0.069 mmol) in methanol (2 mL). The mixture was stirred at room temperature for 63 hours. HCl (5 mL, 1 M) was added and the mixture was stirred for another 15 min. After evaporation of the solvent in vacuo, the residue was suspended in water and extracted with chloroform. The phases were separated and the organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The crude material was purified on a silica gel column using chloroform/EtOH, 95:5, as the eluent to give 24 mg (88% yield) of the product as a pale yellow solid: mp 213-216° C.; MS (TSP) m/z 394 (M+1), 1H NMR (400 MHz, DMSO-d6) δ 9.87 (d, J=5.9 Hz, 1 H), 9.43 (s, 1 H), 8.43 (s, 1 H), 8.23 (d, J=5.48 Hz, 1 H), 7.58 (d, J=9.0 Hz, 1 H), 7.46 (d, J=8.4 Hz, 2 H), 7.29 (m, 1 H), 7.23 (m, 2 H), 7.20 (d, J=5.5 Hz, 1 H), 7.14 (m, 4 H), 7.04 (m, 1 H), 6.88 (m, 1 H), 5.51 (s, 1 H).

Workup

  1. stirringthe mixture was stirred for another 15 min
  2. customAfter evaporation of the solvent in vacuo
  3. extractionextracted with chloroform
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried (MgSO4)
  6. customthe solvent was evaporated in vacuo
  7. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-6bc772ffb0ec41cfa62c76a468fa8838
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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