(S)-2-aminopropanamide hydrochloride → HCID 58806140, compound

HRID 350949Notes

Reaction equation

HRID 350949 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:12]([NH:14][CH2:15][C:16]([NH:18]C)=[O:17])=[O:13])[CH:5]=[N:4][C:3]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33].Cl.N[C@H:36](C(N)=O)C>>[NH2:18][C:16]([C@@H:15]([NH:14][C:12](=[O:13])[C:11]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:9]([N:6]2[C:7](=[O:8])[C:2]([Br:1])=[C:3]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])[N:4]=[CH:5]2)[CH:10]=1)[CH3:36])=[O:17]

Participants

3

Reactant 2

HCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 210889963-[5-bromo-4-[(2,4-difluorobenzyl)oxy)-6-oxopyrimidin-1(6H)-yl]-4-methyl-N-{1-[(methylamino)carbonyl]methyl}benzamide

Product 1

HCID 58806140HCID 58806140, compoundYield 40%

Procedure

The title compound was prepared by a procedure similar to the one described for 3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-yl]-4-methyl-N-{1-[(methylamino)carbonyl]methyl}benzamide using L-alaninamide HCl (0.33 g 2.5 mmol) as the amine. After reverse phase HPLC purification, the organic extracts were concentrated under reduced pressure and dried in vacuo to afford the desired product (370 mg, 40%) as beige solid. 1H-NMR (CD3OD, 400 MHz) δ 8.32 (s, 1H), 7.95 (m, 1H), 7.83 (dd, 1H, J=2 Hz), 7.62 (m, 1H), 7.54 (d, 1H, J=8.4 Hz), 7.01 (m, 2H), 5.60 (q, 2H, J=12.4 Hz), 4.55 (m, 1H), 2.19 (s, 3H), 1.46 (dd, 3H J=1.2) ES-HRMS m/z 521.0598 (M+H C22H20BrF2N4O4 requires 521.0630).

Workup

  1. customThe title compound was prepared by a procedure similar to the one
  2. customAfter reverse phase HPLC purification
  3. concentrationthe organic extracts were concentrated under reduced pressure
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4c478cc96f1f4746aa96f5f434f31ab2
Source dataset
uspto-grants-2007_02
Patent number
US07183287B2

Reaction notes

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