2-Cyanobenzenesulfonyl Chloride → 2-[(4-{2-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazin-1-yl)sulfonyl]benzonitrile

HRID 1772813Notes

Reaction equation

HRID 1772813 reaction equation
[CH3:1][CH:2]([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][N:21](COCC[Si](C)(C)C)[C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40](Cl)(=[O:42])=[O:41])#[N:33]>>[N:18]1[C:17]2[NH:21][CH:22]=[CH:23][C:16]=2[C:15]([C:13]2[CH:12]=[N:11][N:10]([CH:2]([CH3:1])[CH2:3][N:4]3[CH2:5][CH2:6][N:7]([S:40]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[C:32]#[N:33])(=[O:42])=[O:41])[CH2:8][CH2:9]3)[CH:14]=2)=[N:20][CH:19]=1

Participants

3

Reactant 2

HCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 670549204-[1-(1-methyl-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 581809642-[(4-{2-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazin-1-yl)sulfonyl]benzonitrile

Procedure

This compound was prepared according to the procedure of Example 92, using 4-[1-(1-methyl-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine and 2-cyanobenzenesulfonyl chloride as the starting materials. 1H NMR (300 MHz, DMSO-D6): δ 12.05 (s, 1H); 8.61 (s, 1H); 8.58 (s, 1H); 8.21 (s, 1H); 8.07 (m, 1H); 7.95-7.78 (m, 3H); 7.53 (m, 1H); 6.88 (d, 1H); 4.62 (m, 1H); 2.98 (m, 4H); 2.82 (m, 1H); 2.59 (m, 3H); 2.36 (m, 2H); 1.40 (d, 3H); LCMS calculated for C23H25N8O2S(M+H)+: m/z=477.0.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-f76b9d8c26834953aaf789449e9ca2da
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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