Diisopropylethylamine → HCID 118162140, compound

HRID 1749551Notes

Reaction equation

HRID 1749551 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[C:5]1=[O:14].CCN(C(C)C)C(C)C.[C:24]([C:26]1[C:27]([NH:36][C@@H:37]2[CH2:40][C@H:39]([C:41]([NH2:43])=[O:42])[C:38]2([CH3:45])[CH3:44])=[N:28][C:29](S(C)(=O)=O)=[N:30][CH:31]=1)#[N:25]>O>[C:24]([C:26]1[C:27]([NH:36][C@@H:37]2[CH2:40][C@H:39]([C:41]([NH2:43])=[O:42])[C:38]2([CH3:45])[CH3:44])=[N:28][C:29]([NH:1][CH2:2][CH2:3][CH:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH3:13])[C:5]2=[O:14])=[N:30][CH:31]=1)#[N:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 34866213-(2-Aminoethyl)-1-methyl-1,3-dihydro-2H-indol-2-oneHCID 118162146HCID 118162146, compound

Product 1

HCID 118162140HCID 118162140, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

3-(2-Aminoethyl)-1-methylindolin-2-one (231 mg, 1.02 mmol) and DIEA (197 mg, 1.53 mmol) were added to the reaction mixture of (1S,3R)-3-(5-cyano-2-(methylsulfonyl)pyrimidin-4-ylamino)-2,2-dimethylcyclobutanecarboxamide (prepared as described above) at 0° C. and stirred at 90° C. for 1 h. The reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford the crude product, which was purified by standard methods to afford the title compound (17.7 mg, 0.041 mmol, 8% yield over two steps). 1H NMR (400 MHz, CD3OD) δ (ppm) 8.12-8.01 (m, 1H), 7.42-7.33 (m, 2H), 7.17-6.93 (m, 2H), 4.36-4.09 (m, 1H), 3.62-3.60 (m, 2H), 3.23-3.13 (m, 4H), 2.60-2.25 (m, 5H), 1.39-0.88 (m, 6H). MS (ESI) m/z 433.8 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated
  4. customto afford the crude product, which
  5. customwas purified by standard methods

Sources & evidence

ORD record
ord-aa5014c57bcc456ea84d354d44566b20
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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