N-BOC-ethylenediamine → HCID 66623051, compound

HRID 409808Notes

Reaction equation

[Cl:1][C:2]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:3]=1[CH2:4][NH:5][C:6](=[O:29])[N:7]([CH:9]([CH2:25][CH2:26][CH:27]=O)[CH2:10][O:11][C:12](=[O:24])[NH:13][C:14]1[N:15]=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:8].[C:35]([O:39][C:40](=[O:45])[NH:41][CH2:42][CH2:43][NH2:44])([CH3:38])([CH3:37])[CH3:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CC(O)=O>[C:35]([O:39][C:40]([NH:41][CH2:42][CH2:43][NH:44][CH2:27][CH2:26][CH2:25][CH:9]([N:7]([CH3:8])[C:6]([NH:5][CH2:4][C:3]1[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:2]=1[Cl:1])=[O:29])[CH2:10][O:11][C:12](=[O:24])[NH:13][C:14]1[N:15]=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:45])([CH3:38])([CH3:36])[CH3:37]

Participants

Conditions

Temperature: 24 °C

Procedure

To a solution of isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-5-oxo-pentyl ester (0.8 g crude mixture, 1.64 mmol) in anhydrous DCE (3 mL) and AcOH (0.1 mL) was added (2-Amino-ethyl)-carbamic acid tert-butyl ester at 24° C. After 10 h of stirring at 24° C., sodium triacetoxyborohydride (1.05 g, 4.92 mmol) was added in one portion. The slurry was stirred for 2 h at 24° C., quenched with methanol and concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give isoquinolin-3-yl-carbamic acid 5-(2-tert-butoxycarbonylamino-ethylamino)-2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-pentyl ester (0.25 g, 25%) LRMS (M+H+) m/z 631.2.

Workup

stirringThe slurry was stirred for 2 h at 24° C.
customquenched with methanol
concentrationconcentrated
customThe resulting residue was purified on RP-HPLC
additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record: ord-09be03cc7a064b6a9bde59e3e63d2965
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759374B2

Reaction notes

Loading…