Dimethylformamide → HCID 59239476, compound

HRID 1698032Notes

Reaction equation

HRID 1698032 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH2:29][CH3:30])[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].CN(C)C=O.[O:36]1[CH2:39][C:38](=O)[CH2:37]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH2:29][CH3:30])[C:16]3[CH2:22][CH2:21][N:20]([CH:38]4[CH2:39][O:36][CH2:37]4)[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 67178678HCID 67178678, compound

Product 1

HCID 59239476HCID 59239476, compound

Conditions

Temperature
50 °C

Procedure

(S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0500 g, 0.122 mmol) in dry N,N-Dimethylformamide (0.593 mL, 7.66 mmol) at 0° C. was added 3-oxetanone (0.00881 mL, 0.122 mmol). The reaction mixture was stirred at 50° C. for 10 minutes then cooled at 0° C. and added Sodium triacetoxyborohydride (0.05163 g, 0.2436 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was filtered through a disc filter and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.61 (s, 1H), 8.14 (d, J=8.7, 2H), 7.46 (d, J=8.7, 2H), 6.15 (t, J=5.5, 1H), 4.64 (t, J=6.2, 2H), 4.59-4.50 (m, 2H), 3.97 (s, 1H), 3.86 (d, J=10.7, 1H), 3.78 (d, J=11.2, 1H), 3.74-3.60 (m, 4H), 3.55 (t, J=10.9, 1H), 3.43 (d, J=10.4, 1H), 3.35 (d, J=17.0, 1H), 3.18-3.05 (m, 2H), 2.76 (s, 1H), 2.68 (d, J=11.2, 1H), 2.60 (d, J=15.2, 1H), 2.41-2.30 (m, 1H), 1.87-1.67 (m, 2H), 1.06 (t, J=7.2, 3H), 0.83 (t, J=7.4, 3H). LC/MS-m/z+467.2 (M+H)+.

Workup

  1. temperaturethen cooled at 0° C.
  2. temperatureto warm slowly to room temperature
  3. stirringstirred overnight
  4. filtrationThe reaction mixture was filtered through a disc
  5. filtrationfilter
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-447f97452a6648ad92454618d508fe86
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

Loading…