1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-Amino-N-{4-[(4-methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-propionamide

HRID 1876224Notes

Reaction equation

HRID 1876224 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:10](=[O:33])[NH:11][CH2:12][C:13]1[N:22]=[C:21]([N:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH3:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH3:9])(C)(C)C.NCC1N=C(N(C2C=CC(OC)=CC=2)C)C2C(=CC=CC=2)N=1.N(C(OC(C)(C)C)=O)[C@@H](C(O)=O)C.CCN=C=NCCCN(C)C.C(N(C(C)C)C(C)C)C>CN(C=O)C>[NH2:7][C@H:8]([CH3:9])[C:10]([NH:11][CH2:12][C:13]1[N:22]=[C:21]([N:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH3:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)=[O:33]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 44555457(2-Aminomethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amineHCID 59237284[(R)-1-({4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 59242019(R)-2-Amino-N-{4-[(4-methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[(R)-1-({4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-carbamoyl)-ethyl]-carbamic acid tert-butyl ester: The title compound was prepared from (2-aminomethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (100 mg, 0.37 mmol), Boc-D-Ala-OH (70 mg, 0.37 mmol), EDCI (86 mg, 0.45 mmol), HOBt-hydrate (68 mg, 0.82 mmol) and ethyl-diisopropyl-amine (191 μL, 1.1 mmol) in DMF (1.2 mL) by a procedure similar to the preparation of Example 238a and was isolated as a yellow solid, 114 mg (67%). 1H NMR (MeOH-d4) δ 7.7 (d, 1H), 7.62-7.57 (m, 1H), 7.18 (d, 2H), 7.06-6.98 (m, 4H), 4.55 (m, 2H), 4.2 (q, 1H), 3.82 (s, 3H), 3.62 (s, 3H), 1.49 (s, 9H), 1.48 (d, 3H); LC-MS (ESI+; 466 ([M+H]+)).

Workup

  1. customwas isolated as a yellow solid, 114 mg (67%)

Sources & evidence

ORD record
ord-ac1060caaf1146f3937862d41ac6b1bf
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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