1-[5-(2-cyanopropan-2-yl)-2,3-dihydro-1H-inden-1-yl]-3-(1H-indazol-4-yl)urea → n-[(1r)-5-(1-Cyano-1-methylethyl)-2,3-dihydro-1h-inden-1-yl]-n'-1h-indazol-4-ylurea

HRID 656459Notes

Reaction equation

HRID 656459 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11]([NH:15][C:16]([NH:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=1[CH:21]=[N:22][NH:23]3)=[O:17])[CH2:10][CH2:9]2)([CH3:5])[CH3:4])#[N:2]>CO>[C:1]([C:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C@H:11]([NH:15][C:16]([NH:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=1[CH:21]=[N:22][NH:23]3)=[O:17])[CH2:10][CH2:9]2)([CH3:5])[CH3:4])#[N:2]

Participants

3

Reactant 1

HCID 671873051-[5-(2-cyanopropan-2-yl)-2,3-dihydro-1H-inden-1-yl]-3-(1H-indazol-4-yl)urea

Product 1

HCID 11164247n-[(1r)-5-(1-Cyano-1-methylethyl)-2,3-dihydro-1h-inden-1-yl]-n'-1h-indazol-4-ylurea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by chiral separation of the corresponding racemic compound 1-[5-(cyano-isopropyl)-indan-1-yl]-3-(1H-indazol-4-yl)-urea (Ex. 57E) using a chiral column ChiralCel OD. [α]D: +35.4° (c: 1.04, MeOH). MS (ESI) m/z: 360.07 [M+H]+. 1H NMR (DMSO-d6) □: 1.69 (s, 6H), 1.87 (m, 1H), 2.47 (m, 1H), 2.89 (m, 1H), 2.98 (m, 1H), 5.19 (q, 1H), 6.73 (d, 1H), 7.08 (d, 1H), 7.22 (t, 1H), 7.39 (s, 2H), 7.44 (s, 1H), 7.66 (d, 1H), 8.04 (s, 1H), 8.59 (s, 1H), 13.00 (s, 1H). Anal Calcd for C21H21N5O.0.3H2O: C, 69.14; H, 5.97; N, 19.20. Found: C, 69.08; H, 5.95; N, 19.31.

Sources & evidence

ORD record
ord-61c35c9d5acf4662bd1de24f3c31c9ff
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

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