Diisopropylethylamine → HCID 49784830, compound

HRID 2096258Notes

Reaction equation

HRID 2096258 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:5][N:4]=1.[N:21]1([CH2:30][C:31](O)=[O:32])[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[CH:23]=[CH:22]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][N:18]([C:31](=[O:32])[CH2:30][N:21]3[C:25]4=[N:26][CH:27]=[CH:28][CH:29]=[C:24]4[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22139374(1H-Pyrrolo[2,3-b]pyridin-1-yl)acetic acidHCID 59564419HCID 59564419, compound

Product 1

HCID 49784830HCID 49784830, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-methoxy-5-(2-piperazin-1-yl-phenyl)-pyrimidine (7.4 g, 27.37 mmol) dissolved in dichloromethane (100 mL) is added pyrrolo[2,3-b]pyridin-1-yl-acetic acid (4.82 g, 27.37 mmol), TBTU (8.79 g, 27.37 mmol), and DIPEA (14.66 mL, 82.12 mmol). The reaction is stirred for 16 h at ambient temperature. The product is purified on a 100 g Biotage SNAP column with 40% EtOAc in hexanes to provide the title compound (8.3 g, 19.37 mmol, 71% yield).

Workup

  1. customThe product is purified on a 100 g Biotage SNAP column with 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-4eff9712e0614666a6a0aae2df1d8796
Source dataset
uspto-grants-2013_05
Patent number
US08450317B2

Reaction notes

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