Aniline → 4-{4-[3-(4-Dimethylamino-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

HRID 589491Notes

Reaction equation

HRID 589491 reaction equation
NC1C=CC=CC=1.[CH3:8][N:9]([CH3:36])[C:10]([N:12]1[CH2:17][CH:16]=[C:15]([C:18]2[NH:35][C:21]3[N:22]=[CH:23][N:24]=[C:25]([C:26]4[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([NH2:33])[C:27]=4[CH3:34])[C:20]=3[CH:19]=2)[CH2:14][CH2:13]1)=[O:11].CCN(C(C)C)C(C)C.[CH3:46][N:47]([CH3:57])[C:48]1[CH:56]=[CH:55][C:51]([C:52](Cl)=[O:53])=[CH:50][CH:49]=1>C(Cl)Cl.N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:36][N:9]([CH3:8])[C:10]([N:12]1[CH2:13][CH:14]=[C:15]([C:18]2[NH:35][C:21]3[N:22]=[CH:23][N:24]=[C:25]([C:26]4[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([NH:33][C:52](=[O:53])[C:51]5[CH:50]=[CH:49][C:48]([N:47]([CH3:46])[CH3:57])=[CH:56][CH:55]=5)[C:27]=4[CH3:34])[C:20]=3[CH:19]=2)[CH2:16][CH2:17]1)=[O:11]

Participants

7

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 867309834-[4-(3-Amino-5-fluoro-2-methyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

Product 1

HCID 712309114-{4-[3-(4-Dimethylamino-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21875418Pyridine methylene chlorideSolvent

Procedure

To a solution of aniline Intermediate 6 (84 mg, 0.213 mmol) in DCM/pyridine (2:1, 30 ml) were added DIPEA (0.372 ml, 2.13 mmol), 4-dimethylaminobenzoyl chloride (43 mg, 0.234 mmol), and DMAP (2.6 mg, 0.021 mmol). The resulting mixture was stirred at room temperature for 75 hrs. The solvents were removed in vacuo and the resulting mixture was purified by reversed phase HPLC (MeCN/H2O) to afford Example 15.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe resulting mixture was purified by reversed phase HPLC (MeCN/H2O)
  3. customto afford Example 15

Sources & evidence

ORD record
ord-aaee8eeac4e4474d826b1d814f3c5335
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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