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

HRID 17157
Notes
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Reaction equation

HRID 17157 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 Acid
Catalyst
HCID 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, 0.166 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-4ea3bea0673446cc8ce2b48805104bcb
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737160B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes