Formaldehyde → HCID 25017138, compound

HRID 1686053Notes

Reaction equation

HRID 1686053 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2([CH2:9][O:10][C:11]3[CH:20]=[C:19]4[C:14]([C:15]([O:21][C:22]5[C:23]([F:32])=[C:24]6[C:28](=[CH:29][CH:30]=5)[NH:27][C:26]([CH3:31])=[CH:25]6)=[CH:16][CH:17]=[N:18]4)=[CH:13][C:12]=3[O:33][CH3:34])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:39](C)=O.[Na+]>C(Cl)Cl>[CH:1]1([CH2:4][N:5]([CH3:39])[C:6]2([CH2:9][O:10][C:11]3[CH:20]=[C:19]4[C:14]([C:15]([O:21][C:22]5[C:23]([F:32])=[C:24]6[C:28](=[CH:29][CH:30]=5)[NH:27][C:26]([CH3:31])=[CH:25]6)=[CH:16][CH:17]=[N:18]4)=[CH:13][C:12]=3[O:33][CH3:34])[CH2:7][CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 25017408HCID 25017408, compound

Product 1

HCID 25017138HCID 25017138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 27 (50 mg) was mixed with HCHO (2 eq, 37% in H2O), NaBH(OAc)3 (2 eq) in DCM (5 ml) and stirred at RT for 3 hours. The reaction was evaporated and purified with silica gel column to give the titled product (20 mg). Mass: (M+1), 476

Workup

  1. customThe reaction was evaporated
  2. custompurified with silica gel column

Sources & evidence

ORD record
ord-d21c5d7bc9f34c82ac9e8d321a0f7697
Source dataset
uspto-grants-2012_04
Patent number
US08148532B2

Reaction notes

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