Acetic Acid → HCID 86607168, compound

HRID 602506Notes

Reaction equation

HRID 602506 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[S:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19].C=O.[C:25](O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:9][C:10]2[S:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[CH3:25])[CH:5]=[CH:4][C:3]=1[NH:16][C:17](=[O:22])[C:18]([F:19])([F:20])[F:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86607167HCID 86607167, compound

Product 1

HCID 86607168HCID 86607168, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of N-{2-Chloro-4-[(5-chloro-thiophen-2-ylmethyl)-amino]-phenyl}-2,2,2-trifluoroacetamide (3.28 g, 8.88 mmol), 37% aqueous formaldehyde (5 mL), and acetic acid (3 mL), sodium cyanoborohydride (NaBH3CN) (1.1 g) in methanol (10 mL) was added dropwise with stirring during 30 minutes. The reaction mixture was allowed to stand at room temperature for 2 hours and poured into water. After the oil solidified, it was filtered, washed with water and dried in vacuo to give 3.26 g of pale yellow-brown solid. Yield 95%. 1H NMR (DMSO-d6): 2.97 (s, 3H, NMe), 4.72 (s, 2H), 6.82 (m, 1H), 6.91 (m, 2H), 6.97 (d, 1H), 7.21 (d, 1H), 10.92 (br. s, 1H, NHCO). LC/MS (m/z) 382.0 (M+); RT=3.66, (UV, ELSD) 85%, 98%.

Workup

  1. additionwas added dropwise
  2. waitto stand at room temperature for 2 hours
  3. filtrationit was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-80ebbc42d32e470bb3bcfcd5cb185fa6
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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