N-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}-D-alaninamide → (5R)-3-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}-5-ethyl-2,4-imidazolidinedione

HRID 527690Notes

Reaction equation

HRID 527690 reaction equation
CC1(C)C2C(OC3N=CC(NC(=O)[C@@H](C)N)=CC=3)=CC=CC=2[O:4][CH2:3]1.[NH2:25][C@H:26]([CH2:48][CH3:49])[C:27]([NH:29][C:30]1[CH:31]=[N:32][C:33]([O:36][C:37]2[C:42]3[C:43]([CH3:47])([CH3:46])[CH2:44][O:45][C:41]=3[CH:40]=[CH:39][CH:38]=2)=[CH:34][CH:35]=1)=[O:28]>>[CH3:47][C:43]1([CH3:46])[C:42]2[C:37]([O:36][C:33]3[N:32]=[CH:31][C:30]([N:29]4[C:27](=[O:28])[C@@H:26]([CH2:48][CH3:49])[NH:25][C:3]4=[O:4])=[CH:35][CH:34]=3)=[CH:38][CH:39]=[CH:40][C:41]=2[O:45][CH2:44]1

Participants

3

Reactant 2

HCID 67958197N-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}-D-alaninamide2×HCID 86698424(2R)-2-amino-N-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide2×

Product 1

HCID 57410219(5R)-3-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}-5-ethyl-2,4-imidazolidinedione

Procedure

The title compound was made in a similar fashion to the preparation of Example 8 replacing N1-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}-D-alaninamide (Intermediate 61) with (2R)-2-amino-N-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide (Intermediate 63, 57 mg). This afforded the title compound as a white solid (40 mg).

Sources & evidence

ORD record
ord-77c15bfe8d9b4efe8e73e5bcde24903f
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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