Methyl 1-amino-4-bromonaphthalene-2-carboxylate → 3-[(1S,2S)-2-Hydroxycyclohexyl]-4-oxo-3,4-dihydropyrido[3,4-h]quinazoline-6-carbaldehyde

HRID 390320Notes

Reaction equation

HRID 390320 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]3[CH:24]=[CH:23]C=[CH:21][C:13]3=[C:14]([CH:19]=[O:20])[CH:15]=2)[N:10]=[CH:9]1.[NH2:25]C1C2C(=CC=CC=2)C(Br)=CC=1C(OC)=O>>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]3[CH:24]=[CH:23][N:25]=[CH:21][C:13]3=[C:14]([CH:19]=[O:20])[CH:15]=2)[N:10]=[CH:9]1

Participants

3

Reactant 2

HCID 58431835Methyl 1-amino-4-bromonaphthalene-2-carboxylateHCID 866724853-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazoline-6-carbaldehyde

Product 1

HCID 866724843-[(1S,2S)-2-Hydroxycyclohexyl]-4-oxo-3,4-dihydropyrido[3,4-h]quinazoline-6-carbaldehyde

Procedure

3-[(1S,2S)-2-Hydroxycyclohexyl]-4-oxo-3,4-dihydropyrido[3,4-h]quinazoline-6-carbaldehyde was prepared by the procedure described for the synthesis of 3-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazoline-6-carbaldehyde in Example 2, substituting methyl 5-amino-8-bromoisoquinoline-6-carboxylate for methyl 1-amino-4-bromo-2-naphthoate.

Sources & evidence

ORD record
ord-862684922f004564bff45336f35d7477
Source dataset
uspto-grants-2013_02
Patent number
US08383638B2

Reaction notes

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