Acetic Acid → HCID 67253544, compound

HRID 2068289Notes

Reaction equation

HRID 2068289 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH:16]=O)=[CH:15][C:10]=3[N:9]=[C:8]2[NH:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][C:33]=4[O:34][CH3:35])[CH:26]=3)[N:21]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[N:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH2:16][N:44]4[CH2:49][CH2:48][O:47][CH2:46][CH2:45]4)=[CH:15][C:10]=3[N:9]=[C:8]2[NH:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][C:33]=4[O:34][CH3:35])[CH:26]=3)[N:21]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:42])([CH3:41])[CH3:43])[N:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 86654791HCID 86654791, compound

Product 1

HCID 67253544HCID 67253544, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 20 mL vial was added 1-cyclohexyl-2-(5-(4-methoxypyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1H-benzo[d]imidazole-5-carbaldehyde (28 mg, 0.047 mmol.), morpholine (10 mg, 0.11 mmol) and methylene chloride (2 mL). A catalytic amount of acetic acid was added and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (30 mg, 0.14 mmol) was then added and the reaction mixture stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride and washed with water, saturated sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated to give the title compound (15 mg) which was used directly in the next step.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. washwashed with water, saturated sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16db29bf2b24450eb9002235d85daadf
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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