(S)-alpha-amino-cyclopropanepropanamide → 6-Cyclopropylmethoxy-5-(tetrahydro-furan-3-yl)-pyridine-2-carboxylic acid ((S)-1-carbamoyl-2-cyclopropyl-ethyl)-amide

HRID 632174Notes

Reaction equation

HRID 632174 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[CH:15]2[CH2:19][CH2:18][O:17][CH2:16]2)[CH2:3][CH2:2]1.C1(COC2N=C(C(O)=O)C=CC=2C2CCCO2)CC1.[NH2:39][C@@H:40]([CH2:44][CH:45]1[CH2:47][CH2:46]1)[C:41]([NH2:43])=[O:42]>>[C:41]([C@@H:40]([NH:39][C:12]([C:10]1[CH:9]=[CH:8][C:7]([CH:15]2[CH2:19][CH2:18][O:17][CH2:16]2)=[C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[N:11]=1)=[O:14])[CH2:44][CH:45]1[CH2:47][CH2:46]1)(=[O:42])[NH2:43]

Participants

4

Reactant 3

HCID 53964035(S)-alpha-amino-cyclopropanepropanamideHCID 710873686-(Cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acidHCID 710873756-(Cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid

Product 1

HCID 711056186-Cyclopropylmethoxy-5-(tetrahydro-furan-3-yl)-pyridine-2-carboxylic acid ((S)-1-carbamoyl-2-cyclopropyl-ethyl)-amide

Procedure

The title compound was synthesized in analogy to Example 1, using the mixture of 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid and 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid (mixture from Example 114 d), and (S)-2-amino-3-cyclopropyl-propionamide (CAN 156077-93-9) as starting materials, MS (EI): m/e=374.2 [M+H]+.

Sources & evidence

ORD record
ord-3e709f67c0ad49cfaf7233d885fd954a
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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