Methanol → HCID 24961040, compound

HRID 2196601Notes

Reaction equation

HRID 2196601 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1.S1C=CN=C1NC(=O)O[C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=O)=CC=1.CC[N:43]([CH:47](C)C)C(C)C.C[OH:51]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([NH:22][C:47]([NH:43][C:34]2[CH:35]=[C:36]([CH3:31])[O:39][N:37]=2)=[O:51])[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 156927894-Nitrophenyl 1,3-thiazol-2-ylcarbamateHCID 59756883HCID 59756883, compound

Product 1

HCID 24961040HCID 24961040, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-amine (150 mg, 0.50 mmol) and 4-nitrophenyl thiazol-2-ylcarbamate (144 mg, 0.55 mmol) in DCM (5 mL) was added DIPEA (173 uL, 1.00 mmol) at RT. The mixture was allowed to stir for 15 h before the solution was concentrated in vacuo. Purification by prep TLC plate using 15:1 DCM:MeOH yielded the desired compound 1-(1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-yl)-3-(5-methylisoxazol-3-yl)urea (80 mg, 0.19 mmol, 38% yield). MS (ESI pos. ion) m/z: 426.2 (MH+). Calc'd exact mass for C22H27N5O4: 425. 1HNMR (400 MHz, CDCl3): 8.66-8.67 (d, J=4.4 Hz, 1H), 8.36 (bs, 1H), 7.60 (s, 1H), 7.45 (s, 1H), 7.27-7.28 (m, 1H, covered by residual solvent), 5.83 (s, 1H), 4.05 (s, 6H), 3.87 (s, 2H), 3.83-3.85 (m, 1H), 2.83-2.85 (bd, J=10.0 Hz, 2H), 2.37 (s, 3H), 2.31-2.36 (bt, J=10.4 Hz, 2H overlapping), 1.99-2.02 (bd, J=11.2 Hz, 2H), 1.58-1.66 (m, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customPurification by prep TLC plate

Sources & evidence

ORD record
ord-528974f60992466b8a562314dd4dde03
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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