Hydrochloric Acid → 2-hydroxy-1-(4-((2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepin-9-yl)methyl)piperazin-1-yl)ethanone

HRID 1629164Notes

Reaction equation

HRID 1629164 reaction equation
Cl.[OH:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].[CH:12]([N:15]1[C:19]([C:20]2[CH:21]=[C:22]3[N:28]([N:29]=2)[C:27]2[CH:30]=[C:31]([CH:34]=O)[CH:32]=[CH:33][C:26]=2[O:25][CH2:24][CH2:23]3)=[N:18][CH:17]=[N:16]1)([CH3:14])[CH3:13]>C(OCC)C>[OH:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:34][C:31]2[CH:32]=[CH:33][C:26]3[O:25][CH2:24][CH2:23][C:22]4[N:28]([N:29]=[C:20]([C:19]5[N:15]([CH:12]([CH3:14])[CH3:13])[N:16]=[CH:17][N:18]=5)[CH:21]=4)[C:27]=3[CH:30]=2)[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 185068842-Hydroxy-1-(piperazin-1-yl)ethan-1-oneHCID 582046662-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-9-carbaldehyde

Product 1

HCID 582047252-hydroxy-1-(4-((2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepin-9-yl)methyl)piperazin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the procedure for 128 without the use of HCl in diethyl ether, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-9-carbaldehyde was reacted with 2-hydroxy-1-piperazin-1-yl-ethanone to give 132 as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.95 (s, 1 H); 7.86 (d, J=2.0 Hz, 1 H); 7.28-7.23 (m, 1 H); 7.17 (d, J=8.2 Hz, 1 H); 6.86 (s, 1 H); 5.73-5.60 (m, 1 H); 4.55 (t, J=6.0 Hz, 2 H); 4.15 (s, 2 H); 3.69 (t, J=4.8 Hz, 2 H); 3.64-3.55 (m, 3 H); 3.29 (t, J=4.8 Hz, 2 H); 3.16 (t, J=6.0 Hz, 2 H); 2.55-2.46 (m, 4 H); 1.58 (d, J=6.6 Hz, 6 H). LCMS: RT=5.70 min, M+H+=452

Sources & evidence

ORD record
ord-7e7dd3c1f7db4610b490e6861b29fe06
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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