Formic Acid → HCID 178461757, compound

HRID 1409377Notes

Reaction equation

HRID 1409377 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C@@H:17]([NH:19][C:20]([C:22]3[NH:26][N:25]=[C:24]([C:27]4[N:28]=[CH:29][N:30](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:31]=4)[CH:23]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6]([F:10])[C:7]=1[C:8]#[N:9].C(O)=O.C1COCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C@@H:17]([NH:19][C:20]([C:22]3[NH:26][N:25]=[C:24]([C:27]4[N:28]=[CH:29][NH:30][CH:31]=4)[CH:23]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6]([F:10])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8028TetrahydrofuranHCID 70980768HCID 70980768, compound

Product 1

HCID 178461757HCID 178461757, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into (S)—N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-trityl-1H-imidazol-4-yl)-1H-pyrazole-5-carboxamide (0.139 mmol, 0.095 g) was added 4 ml of a solution containing formic acid (41.8 mmol, 1.926 g), THF (20 ml) and water (1 ml). The resulting mixture was stirred first at RT after which the temperature was raised to 50° C. for 2 h. The solvent was evaporated, ACN was added and evaporated again. This was repeated once more. The crude product was purified by preparative HPLC. 0.0169 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.27 (d, 3H), 4.14 (dd, 1H), 4.45 (dd, 1H), 4-57-4.64 (m, 1H), 6.29 (bs), 6.63 (d, 1H), 6.90 (s, 1H), 7.32 (d, 1H), 7.51 (d, 1H), 7.52 (s, 1H), 7.63 (dd, 1H), 7.73 (d, 1H), 7.84-7.86 (m, 1H) LC-MS: [M+1]=439.0.

Workup

  1. temperaturewas raised to 50° C. for 2 h
  2. customThe solvent was evaporated
  3. additionACN was added
  4. customevaporated again
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-8ac084def04c4f759c647199a7afff4a
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…