(R)-(-)-2-Amino-1-propanol → HCID 69480134, compound

HRID 2364543Notes

Reaction equation

HRID 2364543 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:35])=[C:14]([C:30](OCC)=[O:31])[C:15](=[O:29])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:28])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:36][C@H:37]([CH3:40])[CH2:38][OH:39]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:35])=[C:14]([C:30]([NH:36][C@H:37]([CH3:40])[CH2:38][OH:39])=[O:31])[C:15](=[O:29])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:28])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 69480472HCID 69480472, compound

Product 1

HCID 69480134HCID 69480134, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (2R)-2-amino-1-propanol using methods similar to Example 563 to provide a tan solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.19 (d, J=6.74 Hz, 3 H), 1.65-1.81 (m, 6 H), 2.19 (t, J=5.79 Hz, 2 H), 3.21 (t, J=5.90 Hz, 2 H), 3.37 (t, J=6.95 Hz, 2 H), 3.48 (t, J=5.05 Hz, 2 H), 4.05 (t, J=6.00 Hz, 1 H), 4.14-4.23 (m, 4 H), 5.00 (t, J=5.16 Hz, 1 H), 7.10-7.18 (m, 2 H), 7.37-7.44 (m, 2 H), 7.98 (s, 1 H), 8.56 (d, J=1.26 Hz, 1 H), 10.31-10.39 (m, 1 H), 17.24 (s, 1 H); ES+ MS: 511 (M+H+).

Workup

  1. customto provide a tan solid

Sources & evidence

ORD record
ord-d61c0f2727154d6a82b8f31d69add556
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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