Triethylamine → HCID 86663705, compound

HRID 2044083Notes

Reaction equation

HRID 2044083 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:16]=[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[O:25])=[CH:20][CH:19]=3)[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)[CH2:3]1.[CH3:32][C:33]1[S:37][C:36]([NH:38][C:39](=O)[O:40]C2C=CC=CC=2)=[N:35][CH:34]=1.CCN(CC)CC>C1COCC1>[CH3:32][C:33]1[S:37][C:36]([NH:38][C:39](=[O:40])[NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]3[CH:16]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([C:24]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[O:25])=[CH:20][CH:19]=4)[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=3)[CH2:3]2)=[N:35][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57469779HCID 57469779, compoundHCID 66832821HCID 66832821, compound

Product 1

HCID 86663705HCID 86663705, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-6-(3-aminopiperidin-1-yl)-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide (34 mg, 0.080 mmol) and phenyl 5-methylthiazol-2-ylcarbamate (24.39 mg, 0.104 mmol) in THF (2 mL) was added Et3N (0.015 mL, 0.104 mmol) and capped in a vial and stirred at rt overnight. The reaction mixture was chromatographed (ISCO Companion 40 g silica gel column and eluted with NH4OH/MeOH/CH2Cl2 gradient (4-10%) to give 20 mg of (R)-6-(3-(3-(5-methylthiazol-2-yl)ureido)piperidin-1-yl)-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide as a white solid. LCMS: (M+H)+=565.19. 1H NMR (400 MHz, CDCl3) δ ppm 10.35 (1H, s), 8.36 (1H, br. s.), 7.40 (2H, d, J=8.35 Hz), 7.24 (2H, d, J=8.57 Hz), 6.83 (1H, s), 6.35 (1H, s), 3.31-4.02 (13H, m), 2.30 (3H, s), 1.94 (1H, br. s.), 1.53-1.80 (3H, m).

Workup

  1. customcapped in a vial and
  2. customThe reaction mixture was chromatographed (ISCO Companion 40 g silica gel column
  3. washeluted with NH4OH/MeOH/CH2Cl2 gradient (4-10%)

Sources & evidence

ORD record
ord-e6fedcebbba6468cabee85e1a06a78f0
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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