Acetic Acid → HCID 68899844, compound

HRID 970901Notes

Reaction equation

HRID 970901 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]=O.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][NH:38][CH:39]2[C:48]3[N:47]=[CH:46][CH:45]=[CH:44][C:43]=3[CH2:42][CH2:41][CH2:40]2)[CH:32]=1)(=[O:30])=[O:29].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[NH:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:7]=[C:8]1[CH2:16][N:38]([CH2:37][C:33]1[CH:32]=[C:31]([S:28]([NH:27][CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)(=[O:29])=[O:30])[CH:36]=[CH:35][CH:34]=1)[CH:39]1[C:48]2[N:47]=[CH:46][CH:45]=[CH:44][C:43]=2[CH2:42][CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10136158HCID 10136158, compoundHCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazole

Product 1

HCID 68899844HCID 68899844, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using general procedure B: Reaction of 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-2-carbaldehyde (192 mg, 0.70 mmol), N-Pyridin-2-ylmethyl-3-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzenesulfonamide (284 mg, 0.70 mmol), acetic acid (0.2 mL) and sodium triacetoxyborohydride (442 mg, 2.08 mmol) in THF (7 mL) at room temperature under N2 for 40 min., followed by purification of the crude material by chromatography on silica gel (1:1:98 CH3OH—NH3H2O—CH2Cl2,), afforded the title compound (177 mg, 38%) as a white foam.

Workup

  1. customfollowed by purification of the crude material by chromatography on silica gel (1:1:98 CH3OH—NH3H2O—CH2Cl2,)

Sources & evidence

ORD record
ord-b933235521ff4f92a6d0749b949ffe05
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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