4-Methylmorpholine → HCID 59380386, compound

HRID 2353848Notes

Reaction equation

HRID 2353848 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29]([CH2:31][CH2:32][C:33](O)=[O:34])=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.CN1CCOCC1.ON1C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29]([CH2:31][CH2:32][C:33]([N:40]5[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]5)=[O:34])=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 59380443HCID 59380443, compound

Product 1

HCID 59380386HCID 59380386, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]propanoic acid (25 mg, 0.05 mmol, 1 equiv), 4-methyl piperazine (6 mg, 0.06 mmol, 1.2 equiv), 1-[3-(dimethylaminopropyl)]-3-ethyl carbodiimide (14.1 mg, 0.07 mmol, 1.5 equiv), 4-methyl morpholine (10 mg, 0.1 mmol, 2 equiv) and 1-hydroxybenzotriazole (14 mg, 0.1 mmol, 2 equiv) were mixed in DMF and stirred at rt for 16 h. Water and EtOAc were added and extraction was preformed 3 times. Organic layers was concentrated and purified by preparative TLC using 5% MeOH/DCM to yield a solid product (18.5 mg, 64%). 1H-NMR (DMSO-d6) δ 8.94 (s, 1H), 8.49 (s, 1H), 8.45 (d, 1H), 7.96 (d, 1H), 7.74 (d, 1H), 7.52 (dd, 1H), 7.45 (m, 2H), 7.30 (m, 2H), 7.23 (d, 1H), 7.16 (m, 1H), 5.26 (s, 2H), 3.41 (m, 4H), 2.99 (t, 2H), 2.72 (t, 2H), 2.20 (m, 4H), 2.13 (s, 3H); LCMS RT=2.87 min, [M+H]+=590.2

Workup

  1. extractionextraction
  2. concentrationOrganic layers was concentrated
  3. custompurified by preparative TLC

Sources & evidence

ORD record
ord-7ae9908a848541eab703e0abc6a519e2
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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