Diisopropylethylamine → (3R)-1-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)pyrrolidin-3-ol

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	[(2R)-Pyrrolidin-2-yl]methanol--hydrogen chloride (1/1)	HCID 53229934	—
Reactant	2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol	HCID 136030913	—
Product	(3R)-1-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)pyrrolidin-3-ol	HCID 58204290	34%

Reaction Steps

Following the procedures of 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 (R)-prolinol hydrochloride with added DIPEA (2.2 eq.), were reacted and the crude product recrystallised from methanol to give 371 as a green solid (46 mg, 34%). LCMS: RT=2.26 min, [M+H]+=382. 1H NMR 400 MHz (DMSO-d6) δ: 9.09 (1H, s), 7.88 (1H, d, J=0.63 Hz), 7.82 (1H, s), 5.97-5.96 (1H, m), 5.94 (1H, s), 4.97 (1H, d, J=3.62 Hz), 4.49-4.48 (4H, m), 4.39 (1H, s), 3.53-3.42 (3H, m), 2.02-2.00 (1H, m), 1.90-1.87 (1H, m), 1.48 (6H, d, J=6.60 Hz)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08242104B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-804761138bee44aab4ee075a44b2572d
Source note	uspto-grants-2012_08