Methanol → HCID 58204995, compound

HRID 1629471Notes

Reaction equation

HRID 1629471 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21](O)[N:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].C(OC([N:31]1[CH2:35][C@H:34]([C:36]#[N:37])[CH2:33][C@H:32]1[C:38](=[O:40])[NH2:39])=O)(C)(C)C.CO>C(Cl)Cl>[C:36]([C@H:34]1[CH2:35][N:31]([C:21]2[N:20]=[CH:19][C:16]3[C:17]4[N:11]([CH:10]=[C:9]([C:8]5[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=[CH:6][N:7]=5)[N:18]=4)[CH2:12][CH2:13][O:14][C:15]=3[CH:22]=2)[C@H:32]([C:38]([NH2:39])=[O:40])[CH2:33]1)#[N:37]

Participants

5

Reactant 3

HCID 887MethanolHCID 67050743HCID 67050743, compoundHCID 1360309132-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol

Product 1

HCID 58204995HCID 58204995, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure for Example 339, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol from Example 93 and (2S,4R)-2-carbamoyl-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester were reacted. The crude product was subjected to flash chromatography (SiO2, gradient 0 to 10% methanol in DCM) to give 430 as an off-white solid (41 mg, 72%). LCMS: RT=2.85 min, [M+H]+=435. 1H NMR 400 MHz (DMSO-d6) δ: 9.08 (1 H, s), 7.88 (1 H, d, J=0.63 Hz), 7.85 (1 H, s), 7.56 (1 H, br, s), 7.11 (1 H, br, s), 6.04 (1 H, s), 5.94-5.93 (1 H, m), 4.51 (4 H, d, J=15.42 Hz), 4.44 (1 H, d, J=5.97 Hz), 3.92 (1 H, dd, J=10.05, 7.55 Hz), 3.72 (1 H, t, J=8.49 Hz), 3.61-3.53 (1 H, m), 2.55-2.54 (1 H, m), 2.35 (1 H, ddd, J=12.61, 6.87, 3.63 Hz), 1.47 (6 H, dd, J=6.59, 3.21 Hz)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2af305479d574f7982a44b25578fd0f0
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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