Hydrochloric Acid → (R)-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochloride

HRID 519136Notes

Reaction equation

HRID 519136 reaction equation
C(OC([N:8]1[CH2:11][C:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2/[CH:28]=[CH:29]/OCC)[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:34])[C:19](=[O:33])[NH:20][N:21]=2)([CH3:12])[CH2:9]1)=O)(C)(C)C.[ClH:35]>>[ClH:35].[CH3:34][C@@H:18]1[C:19](=[O:33])[NH:20][N:21]=[C:22]2[N:17]1[C:16]1[CH:15]=[C:14]3[N:13]([C:10]4([CH3:12])[CH2:9][NH:8][CH2:11]4)[CH:29]=[CH:28][C:27]3=[CH:26][C:25]=1[O:24][CH2:23]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 867275243-[(R)-7-((E)-2-ethoxy-vinyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86727525(R)-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochlorideYield 91%

Procedure

To a solution of HCl (4M in EtOAc, 160 mL) was added 3-[(R)-7-((E)-2-ethoxy-vinyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (16 g, 33.9 mmol) at 0° C. and the reaction mixture was stirred for 30 min. The reaction mixture was concentrated in vacuo to give crude (R)-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochloride (10 g, 91%), which was used in the next step without further purification. LC/MS (Table 1, Method 25) Rt=0.627 min; MS m/z: 326 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-82ef6d0a35894239a0d4870dd81193f3
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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