Hydrochloric Acid → (S)-2-Amino-succinic acid 4-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl}ester

HRID 28586Notes

Reaction equation

C([O:5][C:6](=[O:45])[C@@H:7]([NH:37]C(OC(C)(C)C)=O)[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[CH:25]=[C:24]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH2:34][CH3:35])[N:23]=[C:22]([NH2:36])[N:21]=2)=[CH:15][CH:14]=1)=[O:10])(C)(C)C.Cl>>[NH2:36][C:22]1[N:21]=[C:20]([NH:19][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][O:11][C:9](=[O:10])[CH2:8][C@H:7]([NH2:37])[C:6]([OH:45])=[O:5])=[CH:18][CH:17]=2)[CH:25]=[C:24]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[O:33][CH2:34][CH3:35])[N:23]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68987504(S)-2-tert-butoxycarbonylamino-succinic acid 4-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl} ester 1-tert-butyl ester

Product 1

HCID 11225499(S)-2-Amino-succinic acid 4-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl}esterYield 69%

Procedure

Following the method described in Example 64, (S)-2-tert-butoxycarbonylamino-succinic acid 4-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl} ester 1-tert-butyl ester and hydrogen chloride provided the title compound (69% yield). 1H NMR (DMSO-d6) δ 1.39 (t, 3H, J=7.0 Hz, CH3), 3.00-3.03 (m, 2H, CH2), 4.17 (q, 2H, J=6.9 Hz, CH2), 4.24 (s, 1H, CH), 5.16 (s, 2H, CH2), 6.74 (s, 1H, Ar), 7.28 (d, 1H, J=8.9 Hz, Ar), 7.43 (d, 2H, J=8.4 Hz, Ar), 7.61-7.68 (m, 2H, Ar), 7.88 (d, 2H, J=8.0 Hz, Ar), 8.52 (s, 3H), 11.23 (s, 1H), 12.77 (s, 1H).

Sources & evidence

ORD record: ord-16991b3a38114c5c9829b4d47979e139
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Reaction notes

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