4-Aminotetrahydropyran → Rac-n2-(4-methoxy-2,3-dihydro-benzofuran-3-yl)-n5-(tetrahydro-pyran-4-yl)-quinoline-2,5-diamine

HRID 1671570Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](Cl)=[N:7]2.[CH3:13][O:14][C:15]1[C:20]2[C:21](=[N:24]O)[CH2:22][O:23][C:19]=2[CH:18]=[CH:17][CH:16]=1.[NH2:26][CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[CH3:13][O:14][C:15]1[C:20]2[CH:21]([NH:24][C:6]3[CH:5]=[CH:4][C:3]4[C:2]([NH:26][CH:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[CH:11][CH:10]=[CH:9][C:8]=4[N:7]=3)[CH2:22][O:23][C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 4192234-Aminotetrahydropyran

HCID 457894242-Chloro-5-iodoquinoline

HCID 866341844-Methoxy-benzofuran-3-one oxime

Product 1

HCID 44217194Rac-n2-(4-methoxy-2,3-dihydro-benzofuran-3-yl)-n5-(tetrahydro-pyran-4-yl)-quinoline-2,5-diamine

Procedure

The title compound, light yellow foam, MS: m/e=392.3 (M+H+), was prepared in accordance with the general method of example 1 from 5-iodo-2-chloroquinoline, (RS)-4-methoxy-2,3-dihydro-benzofuran-3-ylamine (example 39, step A and B) and commercially available 4-amino-tetrahydropyran.

Sources & evidence

ORD record: ord-0fea1a0db2784758bebeff53bcac8001
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994324B2

Reaction notes

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