Morpholine, 4-(chloroacetyl)- → HCID 58204234, compound

HRID 1190674Notes

Reaction equation

[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:26][N:25]([CH2:27][C:28]([NH2:30])=[O:29])[CH2:24]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].OC(C(F)(F)F)=O.N1CC(C2C=CC3C4N=C(C5N(C(C)C)N=CN=5)SC=4[CH2:51][CH2:52][O:53][C:44]=3[CH:43]=2)C1.ClCC(N1CCOCC1)=O>>[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:24][N:25]([CH2:27][C:28]([N:30]6[CH2:43][CH2:44][O:53][CH2:52][CH2:51]6)=[O:29])[CH2:26]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 74040Morpholine, 4-(chloroacetyl)-

HCID 582042442-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-acetamide

HCID 866523168-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt

Product 1

HCID 58204234HCID 58204234, compound

Procedure

Following the procedure of 319, a suspension of 8-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt 235 (200 mg, 0.42 mmol) and 4-(2-chloroacetyl)morpholine gave 471 isolated as a yellow solid (79 mg, 22%). LCMS: RT=3.17 min, [M+H]+=495. 1H NMR δ (ppm) (DMSO-d6): 8.25 (1H, d, J=8.17 Hz), 8.05 (1H, s), 7.17 (1H, dd, J=8.24, 1.82 Hz), 7.03 (1H, d, J=1.77 Hz), 5.82-5.73 (1H, m), 4.35-4.29 (2H, m), 3.67-3.56 (2H, m), 3.58-3.45 (5H, m), 3.44-3.34 (6H, m), 3.31 (2H, s), 3.16 (2H, t, J=6.11 Hz), 1.50 (6H, d, J=6.59 Hz)

Sources & evidence

ORD record: ord-d0024fe5bab84345a3e489533cf2f939
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673952B2

Reaction notes

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