Diisopropylethylamine → HCID 67110480, compound

HRID 455319Notes

Reaction equation

HRID 455319 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:25]([O:27][CH3:28])=[O:26])=[N:11][C:12]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([O:33][C:34]([NH:36][CH2:37][C:38]1[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:39]=1[O:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45](O)=[O:46])=[O:35])([CH3:32])([CH3:31])[CH3:30].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([C:25]([O:27][CH3:28])=[O:26])=[N:11][C:12]([N:19]2[CH2:24][CH2:23][N:22]([C:45](=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41][O:40][C:39]3[CH:48]=[C:49]([F:52])[CH:50]=[CH:51][C:38]=3[CH2:37][NH:36][C:34]([O:33][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:35])[CH2:21][CH2:20]2)=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67109488HCID 67109488, compoundHCID 67109676HCID 67109676, compound

Product 1

HCID 67110480HCID 67110480, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 8-(benzyloxy)-5-(piperazin-1-yl)-1,6-naphthyridine-7-carboxylate (Example 13; 1.3 mmol), 5-(2-((tert-butoxycarbonylamino)methyl)-5-fluorophenoxy)pentanoic acid (Example 17; 1.6 mmol) and diisopropyl ethylamine (3.9 mmol) in dichloromethane (10 ml) was added HBTU (2.0 mmol). The mixture was stirred overnight. The mixture was washed with saturated NaHCO3, 10% citric acid and brine and dried over Na2SO4. The solvent was removed under vacuum. The residue was purified by flash column chromatography over SiO2 (eluent: methanol/CH2Cl2, 1:100) to afford the title compound (800 mg).

Workup

  1. washThe mixture was washed with saturated NaHCO3, 10% citric acid and brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under vacuum
  4. customThe residue was purified by flash column chromatography over SiO2 (eluent: methanol/CH2Cl2, 1:100)

Sources & evidence

ORD record
ord-7bb95907e4fd4f6f8f4b4fa4459cfde8
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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