Formaldehyde → HCID 12050351, compound

HRID 2303345Notes

Reaction equation

HRID 2303345 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][C@H:26]4[C@@H:31]([CH3:32])[O:30][CH2:29][CH2:28][NH:27]4)[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C=O.[CH3:35]N(CCO)C>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][C@H:26]4[C@@H:31]([CH3:32])[O:30][CH2:29][CH2:28][N:27]4[CH3:35])[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 79022-(Dimethylamino)ethanolHCID 22958917HCID 22958917, compound

Product 1

HCID 12050351HCID 12050351, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the product of Step C (21 mg, 0.048 mmol) in 2 mL ethanol was added formaldehyde (37% in H2O, 20 ul, 0.24 mmol), followed by borane-pyridine complex (12 ul, 0.097 mmol). After stirring overnight, the reaction was treated with dimethylaminoethanol (1 mL) and heated for 2 hours. Solvent was removed in vacuo. Purification by prep-TLC afforded the desired product (120 mg, 83%).1.2(d, J=6.3 Hz, 3H), 1.9(m, 1H), 2.1(m, 2H), 2.4(s, 3H), 2.5(m, 1H), 2.7(m, 1H), 3.4(m, 1H), 3.6(m, 1H), 3.8(m, 1H).

Workup

  1. temperatureheated for 2 hours
  2. customSolvent was removed in vacuo
  3. customPurification

Sources & evidence

ORD record
ord-d96c21ef9b924b61a1e94ef1d678b129
Source dataset
uspto-grants-2002_08
Patent number
US06432980B1

Reaction notes

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