(R)-(-)-2-Amino-1-propanol → HCID 21088983, compound

HRID 1713240Notes

Reaction equation

[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:15]2[CH:16]=[C:17]([CH:25]=[CH:26][C:27]=2[CH3:28])[C:18]([NH:20][C@H:21](C)[CH2:22][OH:23])=[O:19])[C:10](=[O:14])[C:11]=1[CH2:12][CH3:13].N[C@H](C)CO>>[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:15]2[CH:16]=[C:17]([CH:25]=[CH:26][C:27]=2[CH3:28])[C:18]([NH:20][CH2:21][CH2:22][OH:23])=[O:19])[C:10](=[O:14])[C:11]=1[CH2:12][CH3:13]

Participants

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanol

HCID 58806160HCID 58806160, compound

Product 1

HCID 21088983HCID 21088983, compound

Procedure

The title compound was prepared using a procedure similar to that used in Step 5 of the synthesis of 3-[4-[(2,4-difluorobenzyl)oxy]-5-ethyl-6-oxopyrimidin-1(6H)-yl]-N-[(1R)-2-hydroxy-1-methylethyl]-4-methylbenzamide by substituting ethanolamine for (R)-(−)-2-amino-1-propanol. 1H NMR (CD3OD/400 MHz) δ8.19 (s, 1H), 7.90 (m, 1H), 7.73 (s, 1H), 7.57 (q, 1H, J=8.4 Hz), 7.51 (d, 1H, J=8.0 Hz), 7.00 (m, 2H), 5.51 (q, 2H, J=12.4 Hz), 3.69 (t, 2H, J=6.0 Hz), 3.48 (t, 2H, J=5.6 Hz), 2.51 (q, 2H, J=7.6 Hz), 2.17 (s, 3H), 1.05 (t, 3H, J=7.6 Hz). ESHRMS m/z 444.1704 (M+H calculated for C23H24F2N3O4 requires 444.1729).

Sources & evidence

ORD record: ord-226b7e0c46c241688df754dea3f254e3
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795271B2

Reaction notes

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