Hydrochloric Acid → 4-(4-(4-(2-(2-Amino acetamido)acetamido)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid

HRID 2093765Notes

Reaction equation

C(OC([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([NH:16][C:17]1[CH:50]=[CH:49][C:20]([CH2:21][NH:22][C:23]2[N:28]=[C:27]([O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[N:26]=[C:25]([NH:35][C:36]3[CH:48]=[CH:47][C:39]([C:40]([O:42]C(C)(C)C)=[O:41])=[CH:38][CH:37]=3)[N:24]=2)=[CH:19][CH:18]=1)=[O:15])=[O:11])=O)(C)(C)C.Cl.O1CCOCC1>>[NH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][NH:22][C:23]2[N:28]=[C:27]([O:29][CH2:30][C:31]([F:34])([F:32])[F:33])[N:26]=[C:25]([NH:35][C:36]3[CH:37]=[CH:38][C:39]([C:40]([OH:42])=[O:41])=[CH:47][CH:48]=3)[N:24]=2)=[CH:49][CH:50]=1)=[O:15])=[O:11]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 67074084Tert-butyl 4-(4-(4-(2-(2-(tert-butoxycarbonylamino)acetamido)acetamido)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

Product 1

HCID 670743234-(4-(4-(2-(2-Amino acetamido)acetamido)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid

Procedure

tert-butyl 4-(4-(4-(2-(2-(tert-butoxycarbonylamino)acetamido)acetamido)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate and 4 N HCl in Dioxane (2 mL, 8.00 mmol) were stirred for 1 h then concentrated under vacuum to give 4-(4-(4-(2-(2-aminoacetamido)acetamido)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (112 mg) which was carried to the next step without purification.

Workup

concentrationthen concentrated under vacuum

Sources & evidence

ORD record: ord-d20ae23ea8084bf2b748097d845c5b49
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445490B2

Reaction notes

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