Trifluoroacetic acid → HCID 89544888, compound

HRID 2283407Notes

Reaction equation

C(OC(=O)[N:7]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:44])[C:24]2[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[C:26]([C@H:32]([NH:35]C(OC(C)(C)C)=O)[CH2:33][CH3:34])[C:25]=2[F:43])=[CH:19][N:18]=1)CC1C=CC(OC)=CC=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:35][C@@H:32]([C:26]1[C:25]([F:43])=[C:24]([C:23]([C:20]2[CH:19]=[N:18][C:17]([NH2:7])=[CH:22][CH:21]=2)=[O:44])[C:29]([O:30][CH3:31])=[CH:28][CH:27]=1)[CH2:33][CH3:34]

Participants

Conditions

Temperature: 70 °C

Procedure

Step 3 {5-[3-((R)-1-tert-Butoxycarbonylamino-propyl)-2-fluoro-6-methoxy-benzoyl]-pyridin-2-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (0.063 g, 0.1 mmol) treated with TFA (2 ml) in DCM (3 ml) over 48 hours, still PMB group present heated at 70° C. for 3 hours. Reaction evaporated to dryness then triturated with diethyl ether to give [3-((R)-1-Amino-propyl)-2-fluoro-6-methoxy-phenyl]-(6-amino-pyridin-3-yl)-methanone (0.018 g). [M-NH2]+287

Workup

customReaction
customevaporated to dryness
customthen triturated with diethyl ether

Sources & evidence

ORD record: ord-d4a4cc34088f406d8e6127fc457ed1c4
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145354B2

Reaction notes

Loading…