Diethylamine → 7-[(1e)-3-(Diethylamino)-1-propenyl]-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

HRID 2390652Notes

Reaction equation

HRID 2390652 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:24]=[CH:25]/[CH:26]=O)=[CH:4][N:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:42]([NH:44][CH2:45][CH3:46])[CH3:43]>C(O)(=O)C.ClCCCl>[CH2:42]([N:44]([CH2:45][CH3:46])[CH2:26]/[CH:25]=[CH:24]/[C:5]1[C:6]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)[C:7]=2[C:2]([NH2:1])=[N:3][CH:4]=1)[CH3:43]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18450607(2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylaldehyde

Product 1

HCID 184508627-[(1e)-3-(Diethylamino)-1-propenyl]-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of Example 360B (30 mg, 0.080 mmol), sodium triacetoxyborohydride (35 mg, 0.16 mmol), 1 drop of acetic acid, and diethylamine (12 mg, 0166 mmol) in 1,2-dichloroethane (2 mL) was stirred for 2 hours at ambient temperature. The mixture was concentrated and the residue was purified by reverse phase chromatography followed by lyophilization to provide the desired product as the acetate salt. 1H NMR (DMSO-d6, 400 MHz) δ 7.94 (s, 1H), 7.55 (s, 1H), 7.44 (m, 4H), 7.20 (t, 1H), 7.11 (m, 4H), 6.67 (d, 1H), 6.22 (m, 1H), 5.55 (br s, 2H), 3.28 (d, 2H), 2.52 (q, 4H), 1.87 (s, 3H), 1.00 (t, 6H); MS m/e 430.4 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-ae408e72cc2640c19865a08b23d1aad9
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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