Formaldehyde → HCID 86695219, compound

HRID 1504060Notes

Reaction equation

HRID 1504060 reaction equation
Cl.[C:2]([C@@H:5]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][CH:23]([NH:26][CH3:27])[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2)(=[O:4])[NH2:3].C=O.[BH3-][C:42]#N.[Na+]>CO>[C:2]([C@@H:5]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:21][CH2:22][CH:23]([N:26]([CH3:42])[CH3:27])[CH2:24][CH2:25]4)[C:9]=3[C:8]1=2)(=[O:4])[NH2:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86695220HCID 86695220, compound

Product 1

HCID 86695219HCID 86695219, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl N-[(1S)-1-carbamoyl-2-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]ethyl]carbamate hydrochloride (100 mg, 0.18 mmol, 1.00 equiv) in methanol (10 mL) was added HCHO (37%, 2 mL) and stirred for 0.5 h at room temperature. This was followed by the addition of NaBH3CN (33.6 mg, 0.53 mmol, 2.99 equiv) at 0° C. and the resulting solution was allowed to react, with stirring, for an additional 2 h at room temperature. The reaction was then quenched by the addition of 20 mL of water and extracted with 3×50 mL of dichloromethane and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column with CH2Cl2: CH3OH (10:1) to provide benzyl N-[(1S)-1-carbamoyl-2-[(3R)-12-[[4-(dimethylamino)cyclohexyl]oxy]7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]ethyl]carbamate (50 mg, 52%) as a white solid.

Workup

  1. customto react
  2. stirringwith stirring, for an additional 2 h at room temperature
  3. customThe reaction was then quenched by the addition of 20 mL of water
  4. extractionextracted with 3×50 mL of dichloromethane
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27924ebb32244eadb1526d306e4aa79c
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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