(S)-1-methyl-10-((S)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one → (R)-1-Methyl-10-((R)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one

HRID 519158Notes

Reaction equation

HRID 519158 reaction equation
[CH3:1][C@H:2]1[C:15](=[O:16])[NH:14][N:13]=[C:12]2[N:3]1[C:4]1[CH:5]=[C:6]3[N:19]([C@@:20]4([CH3:25])[CH2:24][CH2:23][NH:22][CH2:21]4)[CH:18]=[CH:17][C:7]3=[CH:8][C:9]=1[O:10][CH2:11]2.C(OC(N1CC[C@](NC2C=C3C(=CC=2Br)OCC2N3[C@H](C)C(=O)NN=2)(C)C1)=O)(C)(C)C>>[CH3:1][C@@H:2]1[C:15](=[O:16])[NH:14][N:13]=[C:12]2[N:3]1[C:4]1[CH:5]=[C:6]3[N:19]([C@:20]4([CH3:25])[CH2:24][CH2:23][NH:22][CH2:21]4)[CH:18]=[CH:17][C:7]3=[CH:8][C:9]=1[O:10][CH2:11]2

Participants

3

Reactant 2

HCID 86727551(S)-1-methyl-10-((S)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-oneHCID 86727553(R)-3-((R)-7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86727552(R)-1-Methyl-10-((R)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one

Procedure

Using a similar procedure as described in Example #162, Step F-G, (R)-1-methyl-10-((R)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one (SFC (Table 1, Method 52) Rt=4.593 min 0.015 g, 5%) was prepared from (R)-3-((R)-7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (isomer C, SFC (Table 1, Method 54), Rt=1.752 min, 0.45 g, 0.9 mmol). 1H NMR (400 MHz, DMSO-d6) δ 10.71 (brs, 1H), 7.34 (s, 1H), 7.29 (s, 1H), 7.16 (s, 1H), 6.31 (s, 1H), 5.09 (q, J=6.4 Hz, 1H), 4.54 (d, J=14.8 Hz, 2H), 3.11 (m, 4H), 2.45 (m, 2H), 1.57 (s, 3H), 1.32 (d, J=6.4 Hz, 3H). LC/MS (Table 1, Method 4) Rt=1.363 min; MS (ESI): m/z 340 [M+1]+.

Sources & evidence

ORD record
ord-a4c71f1a9cf641218643445d0d53062e
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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