N,N-Dimethylethylenediamine → HCID 10249893, compound

HRID 856013Notes

Reaction equation

HRID 856013 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([C:21](Cl)=[O:22])[S:19][CH:20]=4)[CH:13]=[N:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH2:37]>ClCCl>[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH:37][C:21]([C:18]1[S:19][CH:20]=[C:16]([C:14]2[CH:13]=[N:12][C:11]3[N:10]([N:9]=[CH:8][C:7]=3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:15]=2)[CH:17]=1)=[O:22]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 58691603HCID 58691603, compound

Product 1

HCID 10249893HCID 10249893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)thiophene-2-carbonyl chloride (5-4, 5.0 mg, 0.015 mmol, 1 equiv), diisopropylethylamine (60 TL, 0.030 mmol, 2.0 equiv), and N,N-dimethylethane-1,2-diamine (41 TL, 0.016 mmol, 1.1 equiv) in dichloromethane (1 mL) was mixed and allowed to stand for 8 hours. The reaction mixture was washed with aqueous half-saturated sodium bicarbonate solution (0.5 mL). The organic layer was dried over sodium sulfate and concentrated to give N-[2-(dimethylamino)ethyl]-4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)thiophene-2-carboxamide (5-5) as a yellow solid. LRMS m/z: Calc'd for C21H22N5OS (M+H) 392.2, found 392.3.

Workup

  1. washThe reaction mixture was washed with aqueous half-saturated sodium bicarbonate solution (0.5 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dceaf38093ac4cdb802e9d751e177abc
Source dataset
uspto-grants-2007_08
Patent number
US07262199B2

Reaction notes

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