Hydrochloric Acid → n-1h-indazol-4-yl-n'-[(1S)-4-piperidin-1-yl-2,3-dihydro-1h-inden-1-yl]urea

HRID 451628Notes

Reaction equation

HRID 451628 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11]([NH:13][CH:14]3[C:22]4[C:17](=[C:18]([N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15]3)=[O:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl>CO>[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11]([NH:13][C@@H:14]3[C:22]4[C:17](=[C:18]([N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15]3)=[O:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 112342231-(1H-Indazol-4-yl)-3-(4-piperidin-1-yl-indan-1-yl)-urea

Product 1

HCID 11372281n-1h-indazol-4-yl-n'-[(1S)-4-piperidin-1-yl-2,3-dihydro-1h-inden-1-yl]urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by chiral separation of the corresponding racemic compound 1-(1H-Indazol-4-yl)-3-(4-piperidin-1-yl-indan-1-yl)-urea (Ex. 56E) using a chiral column ChiralCel OD. [α]D: −98.5° (HCl salt, c: 1.02, MeOH). MS (ESI) m/z: 376.00 [M+H]+. 1H NMR (DMSO-d6) δ: 1.56 (m, 2H), 1.65 (m, 4H), 1.78 (m, 1H), 2.44 (m, 1H), 2.77 (m, 1H), 2.85 (m, 3H), 2.95 (m, 2H), 5.16 (q, 1H), 6.66 (d, 1H), 6.81 (d, 1H), 6.95 (d, 1H), 7.07 (d, 1H), 7.22 (m, 2H), 7.68 (d, 1H), 8.05 (s, 1H), 8.62 (s, 1H), 13.00 (s, 1H). Anal Calcd for C22H25N5O: C, 70.38; H, 6.71; N, 18.65. Found: C, 70.18; H, 6.93; N, 18.42.

Sources & evidence

ORD record
ord-492cd63723174ad9b886ec9d5d0ee52e
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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