Aniline → HCID 86654843, compound

HRID 2039738Notes

Reaction equation

HRID 2039738 reaction equation
[C:1]([C:9]1[C:17]2[C:16]([NH:18][C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=3)C(O)=O)=[N:15][CH:14]=[N:13][C:12]=2[NH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN([C:40]([O:44]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>CN(C=O)C>[C:1]([C:9]1[C:17]2[C:16]([NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:21][C:20]=3[C:40]([NH:61][C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)=[O:44])=[N:15][CH:14]=[N:13][C:12]=2[NH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53258437HCID 53258437, compound

Product 1

HCID 86654843HCID 86654843, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-((5-benzoyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)benzoic acid (25 mg, 0.07 mmol) in DMF (1 mL) was added DIPEA (18 μL, 0.105 mmol), HBTU (32 mg, 0.084 mmol), and aniline (7.6 μL, 0.084 mmol). The reaction was stirred at room temperature for 18 hours. The crude was purified by reverse phase preparative HPLC. M.p.>300° C.; 400 MHz 1HNMR (DMSO-d6) δ 13.04 (s, 1H), 11.50 (s, 1H), 10.34 (s, 1H), 8.50 (s, 1H), 8.33 (t, J=1.6 Hz, 1H), 8.26-8.23 (d, J=8.0 Hz, 1H), 7.99 (d, J=2.4 Hz, 1H), 7.88 (d, J=6.8 Hz, 2H), 7.79 (d, J=7.6 Hz, 1H), 7.69-7.53 (m, 5H), 7.37 (t, J=7.6 Hz, 2H), 7.11 (t, J=6.8 Hz, 1H); LCMS [M+H] 434.

Workup

  1. customThe crude was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-9dada0e8076b4dd695c570ac88d84c4b
Source dataset
uspto-grants-2013_11
Patent number
US08580803B2

Reaction notes

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