Formic Acid → HCID 178461743, compound

HRID 1409420Notes

Reaction equation

HRID 1409420 reaction equation
C(O)=O.[Cl:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:17]=[CH:16][N:15]([CH2:18][C@@H:19]([NH:21][C:22]([C:24]3[NH:28][N:27]=[C:26]([C:29]4[N:30]=[CH:31][N:32](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:33]=4)[CH:25]=3)=[O:23])[CH3:20])[N:14]=2)[CH:8]=[CH:9][C:10]=1[C:11]#[N:12]>O.C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:17]=[CH:16][N:15]([CH2:18][C@@H:19]([NH:21][C:22]([C:24]3[NH:28][N:27]=[C:26]([C:29]4[N:30]=[CH:31][NH:32][CH:33]=4)[CH:25]=3)=[O:23])[CH3:20])[N:14]=2)[CH:8]=[CH:9][C:10]=1[C:11]#[N:12]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 70980978HCID 70980978, compound

Product 1

HCID 178461743HCID 178461743, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Formic acid (452 mmol, 20.82 g) was dissolved in a mixture of water (2 ml) and THF (40 ml). (S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-trityl-1H-imidazol-4-yl)-1H-pyrazole-5-carboxamide (1.508 mmol, 1 g) was added and the resulting mixture was heated to 50° C. for 3 h. The stirring continued for 2 days at RT. The mixture was concentrated. ACN was added and evaporated. This was repeated once more. The crude product was purified by flash chromatography. 0.371 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.14 (d, 3H), 4.23-4.56 (m, 3H), 6.76 (bs, 1H), 6.94 (d, 1H), 7.53 (bs, 1H), 7.76 (s, 1H), 7.83 (d, 1H), 7.95-8.04 (m, 2H), 8.07-8.10 (m, 1H), 8.27 (d, 1H), 12.30 (bs, 1H), 13.40 (bs, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionACN was added
  3. customevaporated
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6b190325bb2e4276bbe58e5bee53e1f3
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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