Reserpine → HCID 178486874, compound

HRID 1690483Notes

Reaction equation

HRID 1690483 reaction equation
Cl.CN(C)CCCN=C=NCC.OC1C=CC=C[N+]=1[O-].[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH3:34])[N:29]=[CH:28][N:27]=[C:26]2[O:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][C:43](O)=[O:44])=[CH:38][CH:37]=1.[NH2:46][C:47]1[NH:51][N:50]=[C:49]([CH3:52])[CH:48]=1.C(N(C(C)C)CC)(C)C.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>CC(N(C)C)=O>[CH3:52][C:49]1[CH:48]=[C:47]([NH:46][C:43](=[O:44])[CH2:42][C:39]2[CH:38]=[CH:37][C:36]([O:35][C:26]3[C:25]4[C:30](=[CH:31][C:32]([O:33][CH3:34])=[C:23]([O:22][CH3:21])[CH:24]=4)[N:29]=[CH:28][N:27]=3)=[CH:41][CH:40]=2)[NH:51][N:50]=1

Participants

8

Reactant 6

HCID 5770ReserpineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669066322-[4-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl]acetic acidHCID 178418690HCID 178418690, compoundHCID 178526252HCID 178526252, compound

Product 1

HCID 178486874HCID 178486874, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.113 g) and 2-hydroxypyridine N-oxide (0.065 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetic acid (0.1 g), 5-amino-3-methylpyrazole (0.058 g), diisopropylethylamine (0.051 ml) and DMA (1 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The resultant reaction mixture was transferred onto a Waters ‘β Basic Hypersil’ reversed-phase preparative HPLC column (5 microns silica, 30 mm diameter, 250 mm length) that was eluted with decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.064 g); 1H NMR: (DMSOd6) 2.18 (s, 3H), 3.64 (s, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 6.25 (s, 1H), 7.24 (d, 2H), 7.38 (s, 1H), 7.41 (d, 2H), 7.55 (s, 1H), 8.53 (s, 1H), 10.53 (br s, 1H), 11.99 (br s, 1H); Mass Spectrum: M+H+ 420.

Workup

  1. customThe resultant reaction mixture
  2. washwas eluted with decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent

Sources & evidence

ORD record
ord-949bc11ab05241648897029174c70d54
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

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