HCID 86713688, compound → HCID 71584812, compound

HRID 1257271Notes

Reaction equation

HRID 1257271 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:31])[N:10]([CH2:29][CH3:30])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([N:18](CC2C=CC(OC)=CC=2)[CH3:19])[CH:12]=3)=[CH:6][C:5]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([CH2:43][N:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)[CH:37]=2)=[O:34])=[C:4]([F:49])[CH:3]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:31])[N:10]([CH2:29][CH3:30])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=3)=[CH:6][C:5]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([CH2:43][N:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)[CH:37]=2)=[O:34])=[C:4]([F:49])[CH:3]=1

Participants

3

Reactant 1

HCID 86713688HCID 86713688, compound

Product 1

HCID 71584812HCID 71584812, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1-(4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(4-fluoro-3-(pyrrolidin-1-ylmethyl)phenyl)urea (135 mg, 0.196 mmol) in TFA (3 mL) was stirred at RT for 3 h. The mixture was concentrated to dryness, treated with EtOAc and satd. NaHCO3 and stirred for 15 min. The resulting solid was collected via filtration and dried to afford 1-(4-chloro-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(4-fluoro-3-(pyrrolidin-1-ylmethyl)phenyl)urea (98 mg, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.19 (br s, 1H), 8.71 (br s, 1H), 8.41 (s, 1H), 8.13 (m, 1H), 7.73 (s, 1H), 7.54-7.48 (m, 2H), 7.27 (m, 1H), 7.04 (m, 2H), 6.23 (s, 1H), 4.13 (q, J=7.2 Hz, 2H), 3.54 (s, 2H), 2.86 (s, 3H), 2.42 (m, 4H), 1.66 (m, 4H), 1.20 (t, J=6.9 Hz, 3H); MS (ESI) m/z: 567.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with EtOAc and satd
  3. stirringNaHCO3 and stirred for 15 min
  4. filtrationThe resulting solid was collected via filtration
  5. customdried

Sources & evidence

ORD record
ord-8ef18bc517b947378944aa52354a14ed
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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