Formaldehyde → HCID 11421747, compound

HRID 2103389Notes

Reaction equation

HRID 2103389 reaction equation
[OH:1][C:2]1([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[O:37][CH:38]=[CH:39][N:40]=3)=[CH:32][N:31]=2)[CH2:7][CH2:6][CH:5]([NH:8][C@H:9]2[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[CH2:10]2)[CH2:4][CH2:3]1.C=O.[C:43](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:1][C:2]1([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[O:37][CH:38]=[CH:39][N:40]=3)=[CH:32][N:31]=2)[CH2:7][CH2:6][CH:5]([N:8]([CH3:43])[C@H:9]2[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=3)[CH2:10]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67011331HCID 67011331, compound

Product 1

HCID 11421747HCID 11421747, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-{2-[(3S)-3-({4-Hydroxy-4-[5-(1,3-oxazol-2-yl)pyridin-2-yl]cyclohexyl}amino)pyrrolidin-1-yl]-2-oxoethyl}-3-(trifluoromethyl)benzamide (45 mg, 0.081 mmol) and 37% aqueous formaldehyde (30 mg, 1.0 mmol) were dissolved in methylene chloride (5.6 mL). The mixture was evaporated to dryness. Then the residue was taken up in THF (1 mL) and sodium triacetoxyborohydride (38 mg, 0.18 mmol) was added. After being stirred at room temperature overnight, the mixture was purified by HPLC to provide the title compound (27 mg). MS (M+H) 572.3.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-025e1752ee6c414aa416bb0510c6f89c
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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