Pyridine → HCID 57633982, compound

HRID 661080Notes

Reaction equation

HRID 661080 reaction equation
[NH2:1][C@@H:2]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[CH2:3][NH:4][C:5]1[S:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13]3)=[CH:8][N:9]=1.N1C=CC=CC=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C(Cl)Cl>[O:19]=[C:14]1[CH2:13][C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:7]3[S:6][C:5]([NH:4][CH2:3][C@@H:2]([NH:1][C:37](=[O:39])[CH3:38])[CH2:20][C:21]4[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=4)=[N:9][CH:8]=3)[CH:11]=2)[NH:15]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23654166HCID 23654166, compound

Product 1

HCID 57633982HCID 57633982, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL round-bottom flask was added Example 42 (30 mg, 69 μmol), pyridine (27 mg, 347 μmol), acetic anhydride (14 mg, 139 μmol), and 2 mL of DCM. After 30 minutes, LC-MS showed that the reaction was complete. The reaction mixture was concentrated and dissolved in 2 mL of MeOH, then purified by preparative LC to give N—((S)-1-(5-(2-oxoindolin-5-yl)thiazol-2-ylamino)-3-(4-(trifluoromethyl)-phenyl)propan-2-yl)acetamide (26 mg, 79% yield). MS m/z: 475 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 1.89 (s, 3H), 2.90 (dd, J=13.99, 9.29 Hz, 1H), 3.08 (dd, J=13.99, 5.18 Hz, 1H), 3.46-3.53 (m, 1H), 3.60 (s, 2H), 3.61-3.67 (m, 1H), 4.41-4.48 (m, 1H), 6.96 (d, J=8.22 Hz, 1H), 7.38 (dd, J=8.12, 1.86 Hz, 1H), 7.46-7.51 (m, 3H), 7.63 (d, J=8.02 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in 2 mL of MeOH
  3. custompurified by preparative LC

Sources & evidence

ORD record
ord-47a0ee467ade4ca68212f16ad385721b
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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