2-chloro-N-(1-methylethyl)acetamide → N-Isopropyl-2-{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

HRID 1849393Notes

Reaction equation

HRID 1849393 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.N1[CH2:41][CH:40](C2C=CC3C4N=C(C5N(C(C)C)N=CN=5)SC=4CCOC=3C=2)[CH2:39]1.C(NC(=O)CCl)(C)C>>[CH:40]([NH:30][C:28](=[O:29])[CH2:27][N:25]1[CH2:24][CH:23]([C:21]2[CH:20]=[CH:19][C:16]3[C:17]4[N:18]=[C:9]([C:8]5[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][N:7]=5)[S:10][C:11]=4[CH2:12][CH2:13][O:14][C:15]=3[CH:22]=2)[CH2:26]1)([CH3:41])[CH3:39]

Participants

4

Reactant 3

HCID 761712-chloro-N-(1-methylethyl)acetamideHCID 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}-acetamideHCID 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 67050512N-Isopropyl-2-{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

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 N-isopropyl-2-chloroacetamide gave 470 isolated as a yellow solid (91 mg, 26%). LCMS: RT=3.31 min, [M+H]+=467. 1H NMR δ (ppm) (DMSO-d6): 8.26 (1 H, d, J=8.18 Hz), 8.05 (1 H, s), 7.40 (1 H, d, J=8.06 Hz), 7.17 (1 H, dd, J=8.24, 1.83 Hz), 6.99 (1 H, d, J=1.78 Hz), 5.83-5.73 (1 H, m), 4.35-4.29 (2 H, m), 3.86-3.80 (1 H, m), 3.69-3.58 (3 H, m), 3.41-3.35 (2 H, m), 3.18 (2 H, d, J=6.73 Hz), 3.00 (2 H, s), 1.50 (6 H, d, J=6.59 Hz), 1.03 (6 H, d, J=6.59 Hz)

Sources & evidence

ORD record
ord-7b39d658488b406e8432f1ff1e58f2f4
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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